N-Benzyl-2,3-oxazolidinone as a Glycosyl Donor for Selective α-Glycosylation and One-Pot Oligosaccharide Synthesis Involving 1,2-cis-Glycosylation
- 28 July 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (33) , 10666-10667
- https://doi.org/10.1021/ja062531e
Abstract
Glycosylation reactions using N-benzyl-2,3-trans-oxazolidinones as the glycosyl donors were shown to be highly α-selective. Advantages of the donor include facile preparation in gram-scale preparation and simple deprotection procedures. Subsequently, a one-pot oligosaccharide synthesis involving 1,2-cis glycosidic linkages was demonstrated using the novel glycosyl donors.Keywords
This publication has 7 references indexed in Scilit:
- Automated synthesis of oligosaccharides as a basis for drug discoveryNature Reviews Drug Discovery, 2005
- N-(Phenylthio)-ε-caprolactam: A New Promoter for the Activation of ThioglycosidesOrganic Letters, 2004
- Extended applications and potential limitations of ring-fused 2,3-oxazolidinone thioglycosides in glycoconjugate synthesisTetrahedron Letters, 2003
- Conformational Locking of the Glycosyl Acceptor for Stereocontrol in the Key Step in the Synthesis of HeparinAngewandte Chemie International Edition in English, 2002
- Structural and serological studies of the related O‐specific polysaccharides of Proteus vulgaris O21 and Proteus mirabilis O48 having oligosaccharide‐phosphate repeating unitsEuropean Journal of Biochemistry, 2000
- Synthesis of Complex Carbohydrates and Glycoconjugates: Enzyme-Based and Programmable One-Pot StrategiesChemical Reviews, 2000
- The azidonitration of tri-O-acetyl-D-galactalCanadian Journal of Chemistry, 1979