The Experts below are selected from a list of 216 Experts worldwide ranked by ideXlab platform
Omar Parve - One of the best experts on this subject based on the ideXlab platform.
-
A chemoenzymatic synthesis of Deoxy Sugar esters involving stereoselective acetylation of hemiacetals catalyzed by CALB
Journal of Molecular Catalysis B: Enzymatic, 2011Co-Authors: Ly Villo, Tonis Pehk, Malle Kreen, Marina Kudryashova, Andrus Metsala, Sven Tamp, Ülo Lille, Omar ParveAbstract:Abstract An extension of the scope of the chemoenzymatic strategy for the synthesis of stereochemically pure pyranose Deoxy Sugar esters of different carboxylic acids has been achieved. The objective of the work was to extend the strategy to the synthesis of furanose Deoxy Sugar derivatives and additionally, to N-Boc-protected amino acid esters. With all used carboxylic acids (Deoxycholic acid, α-methoxyphenylacetic acid, N-Boc- l -phenylalanine and N-Boc- l -tyrosine) the lipase-catalyzed stereoselective acetylation of furanose or pyranose hemiacetal moiety as a key step afforded one desired stereochemically pure acetylated hemiacetal Deoxy Sugar ester in high de.
-
synthesis of Deoxy Sugar esters a chemoenzymatic stereoselective approach affording Deoxy Sugar derivatives also in the form of aldehyde
Journal of Organic Chemistry, 2007Co-Authors: Ly Villo, Tonis Pehk, Malle Kreen, Andrus Metsala, Kady Danilas, Imre Vallikivi, Sirje Vija, Luciano Saso, Omar ParveAbstract:A chemoenzymatic synthesis of Deoxy Sugar esters is described. The synthesis is based on the O-alkylation of carboxylic acid with 2-bromo-5-acetoxypentanal. The method allows treatment of hydroxy carboxylic acids without protection of alcoholic hydroxyl groups. Several stereoisomeric Deoxy Sugar esters were resolved (up to ee or de > 98%) using a lipase-catalyzed acetylation of hemiacetals that in certain cases afforded Deoxy Sugar derivatives in the form of aldehydes. The stereochemistry of the reactions was determined by the NMR spectra of mandelic acid derivatives.
George A Odoherty - One of the best experts on this subject based on the ideXlab platform.
-
de novo synthesis of Deoxy Sugar via a wharton rearrangement
ChemInform, 2012Co-Authors: Hua Yu Leo Wang, George A OdohertyAbstract:A variety of new, rare Deoxy Sugars such as 6-Deoxyallose (IV) and 6-Deoxyfurose (VIII) are synthesized utilizing the Wharton rearrangement of epoxy ketone (I) as the key step.
-
de novo synthesis of Deoxy Sugar via a wharton rearrangement
Chemical Communications, 2011Co-Authors: Hua Yu Leo Wang, George A OdohertyAbstract:A highly divergent synthesis of α-fuco-, α-6-Deoxy-allo-, α-6-Deoxy-altro-pyranosides has been achieved. This route utilizes a Wharton rearrangement as part of a new post-glycosylation transformation strategy.
Ly Villo - One of the best experts on this subject based on the ideXlab platform.
-
A chemoenzymatic synthesis of Deoxy Sugar esters involving stereoselective acetylation of hemiacetals catalyzed by CALB
Journal of Molecular Catalysis B: Enzymatic, 2011Co-Authors: Ly Villo, Tonis Pehk, Malle Kreen, Marina Kudryashova, Andrus Metsala, Sven Tamp, Ülo Lille, Omar ParveAbstract:Abstract An extension of the scope of the chemoenzymatic strategy for the synthesis of stereochemically pure pyranose Deoxy Sugar esters of different carboxylic acids has been achieved. The objective of the work was to extend the strategy to the synthesis of furanose Deoxy Sugar derivatives and additionally, to N-Boc-protected amino acid esters. With all used carboxylic acids (Deoxycholic acid, α-methoxyphenylacetic acid, N-Boc- l -phenylalanine and N-Boc- l -tyrosine) the lipase-catalyzed stereoselective acetylation of furanose or pyranose hemiacetal moiety as a key step afforded one desired stereochemically pure acetylated hemiacetal Deoxy Sugar ester in high de.
-
synthesis of Deoxy Sugar esters a chemoenzymatic stereoselective approach affording Deoxy Sugar derivatives also in the form of aldehyde
Journal of Organic Chemistry, 2007Co-Authors: Ly Villo, Tonis Pehk, Malle Kreen, Andrus Metsala, Kady Danilas, Imre Vallikivi, Sirje Vija, Luciano Saso, Omar ParveAbstract:A chemoenzymatic synthesis of Deoxy Sugar esters is described. The synthesis is based on the O-alkylation of carboxylic acid with 2-bromo-5-acetoxypentanal. The method allows treatment of hydroxy carboxylic acids without protection of alcoholic hydroxyl groups. Several stereoisomeric Deoxy Sugar esters were resolved (up to ee or de > 98%) using a lipase-catalyzed acetylation of hemiacetals that in certain cases afforded Deoxy Sugar derivatives in the form of aldehydes. The stereochemistry of the reactions was determined by the NMR spectra of mandelic acid derivatives.
Hua Yu Leo Wang - One of the best experts on this subject based on the ideXlab platform.
-
de novo synthesis of Deoxy Sugar via a wharton rearrangement
ChemInform, 2012Co-Authors: Hua Yu Leo Wang, George A OdohertyAbstract:A variety of new, rare Deoxy Sugars such as 6-Deoxyallose (IV) and 6-Deoxyfurose (VIII) are synthesized utilizing the Wharton rearrangement of epoxy ketone (I) as the key step.
-
de novo synthesis of Deoxy Sugar via a wharton rearrangement
Chemical Communications, 2011Co-Authors: Hua Yu Leo Wang, George A OdohertyAbstract:A highly divergent synthesis of α-fuco-, α-6-Deoxy-allo-, α-6-Deoxy-altro-pyranosides has been achieved. This route utilizes a Wharton rearrangement as part of a new post-glycosylation transformation strategy.
Jianglong Zhu - One of the best experts on this subject based on the ideXlab platform.
-
direct synthesis of 2 Deoxy β glycosides via anomeric o alkylation with secondary electrophiles
ChemInform, 2014Co-Authors: Danyang Zhu, Kedar N Baryal, Surya Adhikari, Jianglong ZhuAbstract:Biologically interesting 2-Deoxy-β-glycosides can be prepared from 2-Deoxy-Sugar-derived anomeric lactols and secondary triflates as the electrophile.
-
direct synthesis of 2 Deoxy β glycosides via anomeric o alkylation with secondary electrophiles
Journal of the American Chemical Society, 2014Co-Authors: Danyang Zhu, Kedar N Baryal, Surya Adhikari, Jianglong ZhuAbstract:An approach for direct synthesis of biologically significant 2-Deoxy-β-glycosides has been developed via O-alkylation of a variety of 2-Deoxy-Sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-Deoxy-Sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-Deoxy-β-tetrasaccharide.