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Barry V. L. Potter - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of d- and l-Myo-Inositol 2,4,5-trisphosphate and trisphosphorothioate: structural analogues of d-Myo-Inositol 1,4,5-trisphosphate
Carbohydrate Research, 2002Co-Authors: Stephen J. Mills, Barry V. L. PotterAbstract:Abstract The preparation of d - and l -Myo-Inositol 2,4,5-trisphosphate is described, together with the phosphorothioate counterparts. The known chiral diols d - and l -1,4-di-O-benzyl-5,6-bis-O-p-methoxybenzyl-Myo-Inositol were regioselectively protected at the 3-position using a benzyl group via a 2,3-O-stannylene acetal. Removal of the p-methoxybenzyl groups of each enantiomer gave d - and l -1,3,6-tri-O-benzyl-Myo-Inositol. Phosphitylation with bis(benzyloxy)diisoproplyaminophosphine and 1H-tetrazole gave the trisphosphite intermediate for each enantiomer. Oxidation with 3-chloroperoxybenzoic acid gave the fully protected d - and l -Myo-Inositol 2,4,5-trisphosphates. Sulphoxidation of the d - and l -2,4,5-trisphosphite intermediates gave the fully protected d - and l -Myo-Inositol 2,4,5-trisphosphorothioate compounds. The fully protected trisphosphates were deblocked using hydrogenolysis and the phosphorothioates were deprotected using sodium in liquid ammonia. The individual compounds were then purified using ion exchange chromatography to afford pure d - and l -Myo-Inositol 2,4,5-trisphosphates together with the corresponding phosphorothioates.
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Synthesis of the enantiomers of 6-deoxy-Myo-Inositol 1,3,4,5-tetrakisphosphate, structural analogues of Myo-Inositol 1,3,4,5-tetrakisphosphate.
Chemistry: A European Journal, 2001Co-Authors: Graeme Horne, Barry V. L. PotterAbstract:: D-Myo-Inositol 1,3,4,5-tetrakisphosphate [Ins(1,3,4,5)P4] is produced rapidly from the established second messenger D-Myo-Inositol 1,4,5-trisphosphate [Ins(1,4,5)P4] in stimulated cells. Despite extensive investigations, in particular concerning its potential role in mediating cellular Ca2+ influx, no exact cellular function has been described for this inositol phosphate; however, binding sites have been identified in a number of tissues and it has been shown to act synergistically with Ins(1,4,5)P3. To assist in the elucidation of the mechanism of action and structural requirements within the Ins(1,3,4,5)P4 moiety that are necessary for recognition and activation of the receptor, structural analogues of this tetrakisphosphate are required. Routes for the synthesis of racemic 6-deoxy-Myo-Inositol 1,3,4,5-tetrakisphosphate [6-deoxy-DL-Ins(1,3,4,5)P4] and the chiral antipodes D- and L-6-deoxy-Myo-Inositol 1,3,4,5-tetrakisphosphate are described here. The racemic tetrakisphosphate was synthesised from DL-1,2-O-isopropylidene-Myo-Inositol in eight steps. Deoxygenation at C-6 was achieved following the Barton-McCombie procedure. Both chiral tetrakisphosphates were synthesised through resolution of racemic cis-diol 6-deoxy-1,4,5-tri-O-p-methoxybenzyl-Myo-Inositol with the chiral auxiliary (S)-(+)-O-acetylmandelic acid. Absolute configuration was confirmed by synthesis of the known D-6-deoxy-Myo-Inositol. Both D-6-deoxy-Ins(1,3,4,5)P4 and its enantiomer will be useful tools to unravel the enigmatic role of Ins(1,3,4,5)P4 in the polyphosphoinositide pathway of signal transduction.
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Investigation of the inframolecular acid-base properties of D-Myo-Inositol 1,3,4,5-tetrakisphosphate and DL-Myo-Inositol 1,2,4,5-tetrakisphosphate
Chemical Communications, 1997Co-Authors: Philippe Guédat, Barry V. L. Potter, Andrew M. Riley, Gilbert Schlewer, Elisabeth Krempp, Bernard SpiessAbstract:The protonation processes of the individual phosphate groups in two regioisomeric inositol polyphosphates, D-Myo-Inositol 1,3,4,5-tetrakisphosphate and DL-Myo-Inositol 1,2,4,5-tetrakisphosphate, have been investigated by 31 P NMR titration experiments; the results are compared to those from D-Myo-Inositol 1,4,5-trisphosphate.
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Myo-Inositol 1,4,6-trisphosphorothioate and Myo-Inositol 1,3,4-trisphosphorothioate: New synthetic Ca2+-mobilising partial agonists at the inositol 1,4,5-trisphosphate receptor
Bioorganic & Medicinal Chemistry Letters, 1995Co-Authors: Stephen J. Mills, Andrew M. Riley, C T Murphy, Anthony J. Bullock, John Westwick, Barry V. L. PotterAbstract:Abstract Syntheses of myo -inositol 1,4,6-trisphosphorothioate and 1,3,4-trisphosphorothioate from myo -inositol are described; these trisphosphorothioates, derived from structure-activity considerations of myo -inositol 1,3,4,6-tetrakisphosphate, are low intrinsic activity partial agonists at the platelet Ins(1,4,5)P 3 receptor.
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Unambiguous Total Synthesis of the Enantiomers of Myo-Inositol 1,3,4-Trisphosphate: 1L-Myo-Inositol 1,3,4-Trisphosphate Mobilizes Intracellular Ca2+ in Limulus Photoreceptors
Journal of Medicinal Chemistry, 1994Co-Authors: Andrew M. Riley, Richard J. Payne, Barry V. L. PotterAbstract:: Syntheses of the enantiomers of Myo-Inositol 1,3,4-trisphosphate are described. 1,4-Di-O-allyl-Myo-Inositol was regioselectively p-methoxybenzylated at the 3-position to give 1,4-di-O-allyl-3-O-(p-methoxybenzyl)-Myo-Inositol followed by benzylation of the remaining free hydroxyl groups to give the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-Myo-Inositol. Removal of the p-methoxybenzyl and allyl groups gave 2,4,5-tri-O-benzyl-Myo-Inositol which was phosphitylated with bis(benzyloxy)(diisopropylamino)phosphine to give the fully protected trisphosphite triester. Oxidation using tert-butyl hydroperoxide gave 2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-Myo-Inositol, and deprotection using sodium in liquid ammonia gave racemic Myo-Inositol 1,3,4-trisphosphate. Deprotection of the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-Myo-Inositol by isomerization of allyl groups followed by mild acid hydrolysis gave 2,4,5-tri-O-benzyl-1-O-(p-methoxybenzyl)-Myo-Inositol, which was converted to the diastereoisomeric (bis-(-)-camphanates. The diastereoisomers were separated by column chromatography and the camphanates and the p-methoxybenzyl group removed by saponification and acid hydrolysis, respectively, for each diastereoisomer to give the enantiomers of 2,4,5-tri-O-benzyl-Myo-Inositol. The absolute configurations of the latter were established by conversion of 1L-2,5,6-tri-O-benzyl-3-O-(p-methoxybenyl)-Myo-Inositol to the known 1L-1,2,4,5,6-penta-O-benzyl-Myo-Inositol. Phosphorylation and deblocking gave the D- and L-enantiomers of Myo-Inositol 1,3,4-trisphosphate. Biological evaluation in Limulus photoreceptors showed that 1L-Myo-Inositol 1,3,4-trisphosphate was much more active than the D-enantiomer, producing repetitive bursts of depolarization due to mobilization of intracellular calcium.
Mohan M. Bhadbhade - One of the best experts on this subject based on the ideXlab platform.
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Sulfonate Protecting Groups: Synthesis of D‐ and L‐myo‐Inositol‐1,3,4,5‐tetrakisphosphate Precursors by a Novel Silver(I) Oxide‐Mediated O‐Alkylation of 2,4(6)‐Di‐O‐acyl‐6(4)‐O‐sulfonyl‐myo‐Inositol 1,3,5‐Orthoformate Derivatives Through Intramolecul
European Journal of Organic Chemistry, 2003Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M. BhadbhadeAbstract:Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of Myo-Inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of Myo-Inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-Myo-Inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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sulfonate protecting groups synthesis of d and l myo inositol 1 3 4 5 tetrakisphosphate precursors by a novel silver i oxide mediated o alkylation of 2 4 6 di o acyl 6 4 o sulfonyl myo inositol 1 3 5 orthoformate derivatives through intramolecular as
European Journal of Organic Chemistry, 2003Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M. BhadbhadeAbstract:Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of Myo-Inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of Myo-Inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-Myo-Inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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Sulfonate protecting groups. Regioselective sulfonylation of Myo-Inositol orthoesters-improved synthesis of precursors of D- and L-Myo-Inositol 1,3,4,5-tetrakisphosphate, Myo-Inositol 1,3,4,5,6-pentakisphosphate and related derivatives.
Carbohydrate Research, 2002Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Thoniyot Praveen, Mohan M. BhadbhadeAbstract:Abstract The regioselectivity of sulfonylation of Myo-Inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. Monosulfonylation of Myo-Inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in sulfonylation of the 2-hydroxyl group. Disulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of Myo-Inositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding Myo-Inositol orthoester derivative. These new methods of protection–deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-Myo-Inositol, which are precursors for the synthesis of d - and l -Myo-Inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-O-benzyl-Myo-Inositol which is a precursor for the preparation of Myo-Inositol 1,3,4,5,6-pentakisphosphate.
Mysore S. Shashidhar - One of the best experts on this subject based on the ideXlab platform.
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Sulfonate Protecting Groups: Synthesis of D‐ and L‐myo‐Inositol‐1,3,4,5‐tetrakisphosphate Precursors by a Novel Silver(I) Oxide‐Mediated O‐Alkylation of 2,4(6)‐Di‐O‐acyl‐6(4)‐O‐sulfonyl‐myo‐Inositol 1,3,5‐Orthoformate Derivatives Through Intramolecul
European Journal of Organic Chemistry, 2003Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M. BhadbhadeAbstract:Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of Myo-Inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of Myo-Inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-Myo-Inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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sulfonate protecting groups synthesis of d and l myo inositol 1 3 4 5 tetrakisphosphate precursors by a novel silver i oxide mediated o alkylation of 2 4 6 di o acyl 6 4 o sulfonyl myo inositol 1 3 5 orthoformate derivatives through intramolecular as
European Journal of Organic Chemistry, 2003Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M. BhadbhadeAbstract:Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of Myo-Inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of Myo-Inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-Myo-Inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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Sulfonate protecting groups. Regioselective sulfonylation of Myo-Inositol orthoesters-improved synthesis of precursors of D- and L-Myo-Inositol 1,3,4,5-tetrakisphosphate, Myo-Inositol 1,3,4,5,6-pentakisphosphate and related derivatives.
Carbohydrate Research, 2002Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Thoniyot Praveen, Mohan M. BhadbhadeAbstract:Abstract The regioselectivity of sulfonylation of Myo-Inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. Monosulfonylation of Myo-Inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in sulfonylation of the 2-hydroxyl group. Disulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of Myo-Inositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding Myo-Inositol orthoester derivative. These new methods of protection–deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-Myo-Inositol, which are precursors for the synthesis of d - and l -Myo-Inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-O-benzyl-Myo-Inositol which is a precursor for the preparation of Myo-Inositol 1,3,4,5,6-pentakisphosphate.
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Convenient synthesis of 4,6-di-O-benzyl-Myo-Inositol and Myo-Inositol 1,3,5-orthoesters
Carbohydrate Research, 2001Co-Authors: Thoniyot Praveen, Mysore S. ShashidharAbstract:Abstract Convenient high yielding methods for the preparation of 4,6-di- O -benzyl- myo -inositol, myo -inositol 1,3,5-orthoformate and myo -inositol 1,3,5-orthoacetate, without involving chromatography are described. Myo -inositol was converted to racemic 2,4-di- O -benzoyl- myo -inositol 1,3,5-orthoformate by successive treatment with triethyl orthoformate and benzoyl chloride. The dibenzoate obtained on benzylation with benzyl bromide and silver(I) oxide gave 2- O -benzoyl-4,6-di- O -benzyl- myo -inositol 1,3,5-orthoformate. Deprotection of the benzoate and the orthoformate with isobutylamine and aqueous trifluoroacetic acid, respectively gave 4,6-di- O -benzyl- myo -inositol in an overall yield of 67%. Myo -inositol orthoformate and orthoacetate were prepared and isolated as their tribenzoates. The free orthoesters were regenerated by deprotection of the benzoates by aminolysis with isobutylamine.
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Racemic 2,4-di-O-benzoyl-Myo-Inositol 1,3,5-orthoformate: a versatile intermediate for the preparation of Myo-Inositol phosphates
Carbohydrate Research, 1998Co-Authors: Mysore S. ShashidharAbstract:Abstract The versatility of racemic 2,4-di- O -benzoyl- myo -inositol 1,3,5-orthoformate as an intermediate for the preparation of protected myo -inositol derivatives is demonstrated. Procedures described provide simple access to several protected myo -inositol derivatives which are intermediates for the preparation of myo -inositol phosphates and racemic ononitol.
Kana M. Sureshan - One of the best experts on this subject based on the ideXlab platform.
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Sulfonate Protecting Groups: Synthesis of D‐ and L‐myo‐Inositol‐1,3,4,5‐tetrakisphosphate Precursors by a Novel Silver(I) Oxide‐Mediated O‐Alkylation of 2,4(6)‐Di‐O‐acyl‐6(4)‐O‐sulfonyl‐myo‐Inositol 1,3,5‐Orthoformate Derivatives Through Intramolecul
European Journal of Organic Chemistry, 2003Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M. BhadbhadeAbstract:Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of Myo-Inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of Myo-Inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-Myo-Inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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sulfonate protecting groups synthesis of d and l myo inositol 1 3 4 5 tetrakisphosphate precursors by a novel silver i oxide mediated o alkylation of 2 4 6 di o acyl 6 4 o sulfonyl myo inositol 1 3 5 orthoformate derivatives through intramolecular as
European Journal of Organic Chemistry, 2003Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M. BhadbhadeAbstract:Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of Myo-Inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of Myo-Inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-Myo-Inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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Sulfonate protecting groups. Regioselective sulfonylation of Myo-Inositol orthoesters-improved synthesis of precursors of D- and L-Myo-Inositol 1,3,4,5-tetrakisphosphate, Myo-Inositol 1,3,4,5,6-pentakisphosphate and related derivatives.
Carbohydrate Research, 2002Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Thoniyot Praveen, Mohan M. BhadbhadeAbstract:Abstract The regioselectivity of sulfonylation of Myo-Inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. Monosulfonylation of Myo-Inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in sulfonylation of the 2-hydroxyl group. Disulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of Myo-Inositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding Myo-Inositol orthoester derivative. These new methods of protection–deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-Myo-Inositol, which are precursors for the synthesis of d - and l -Myo-Inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-O-benzyl-Myo-Inositol which is a precursor for the preparation of Myo-Inositol 1,3,4,5,6-pentakisphosphate.
Rajesh G. Gonnade - One of the best experts on this subject based on the ideXlab platform.
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Sulfonate Protecting Groups: Synthesis of D‐ and L‐myo‐Inositol‐1,3,4,5‐tetrakisphosphate Precursors by a Novel Silver(I) Oxide‐Mediated O‐Alkylation of 2,4(6)‐Di‐O‐acyl‐6(4)‐O‐sulfonyl‐myo‐Inositol 1,3,5‐Orthoformate Derivatives Through Intramolecul
European Journal of Organic Chemistry, 2003Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M. BhadbhadeAbstract:Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of Myo-Inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of Myo-Inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-Myo-Inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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sulfonate protecting groups synthesis of d and l myo inositol 1 3 4 5 tetrakisphosphate precursors by a novel silver i oxide mediated o alkylation of 2 4 6 di o acyl 6 4 o sulfonyl myo inositol 1 3 5 orthoformate derivatives through intramolecular as
European Journal of Organic Chemistry, 2003Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Mohan M. BhadbhadeAbstract:Alkylation of racemic 2,4-di-O-acyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates mediated by silver(I) oxide affords the corresponding racemic 2,4-di-O-alkyl-6-O-sulfonyl-Myo-Inositol 1,3,5-orthoformates in good yields. Control experiments suggest that these unusual reactions are due to intramolecular assistance by the sulfonyl group. O-Alkylation reactions of Myo-Inositol 1,3,5-orthoformate derivatives provide a new route for the synthesis of important ether derivatives of Myo-Inositol, which are intermediates for the preparation of phosphoinositols. The utility of this method is demonstrated by the preparation of D- and L-2,4-di-O-benzyl-Myo-Inositols, which were obtained by benzylation of 2,4-di-O-benzoyl-6-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate and 2,6-di-O-benzoyl-4-O-camphorsulfonyl-Myo-Inositol 1,3,5-orthoformate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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Sulfonate protecting groups. Regioselective sulfonylation of Myo-Inositol orthoesters-improved synthesis of precursors of D- and L-Myo-Inositol 1,3,4,5-tetrakisphosphate, Myo-Inositol 1,3,4,5,6-pentakisphosphate and related derivatives.
Carbohydrate Research, 2002Co-Authors: Kana M. Sureshan, Mysore S. Shashidhar, Rajesh G. Gonnade, Thoniyot Praveen, Mohan M. BhadbhadeAbstract:Abstract The regioselectivity of sulfonylation of Myo-Inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. Monosulfonylation of Myo-Inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in sulfonylation of the 2-hydroxyl group. Disulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of Myo-Inositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding Myo-Inositol orthoester derivative. These new methods of protection–deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-Myo-Inositol, which are precursors for the synthesis of d - and l -Myo-Inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-O-benzyl-Myo-Inositol which is a precursor for the preparation of Myo-Inositol 1,3,4,5,6-pentakisphosphate.
