An approach to stereoselective preparation of 3-C-glycosylated D- and L-glucals
Language English Country Netherlands Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
20035928
DOI
10.1016/j.carres.2009.11.025
PII: S0008-6215(09)00564-3
Knihovny.cz E-resources
- MeSH
- Disaccharides chemical synthesis MeSH
- Glycosylation MeSH
- Mandelic Acids chemistry MeSH
- Stereoisomerism MeSH
- Vinyl Compounds chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Disaccharides MeSH
- Mandelic Acids MeSH
- mandelic acid MeSH Browser
- vinyl ether MeSH Browser
- Vinyl Compounds MeSH
An approach to stereoselective synthesis of alpha- or beta-3-C-glycosylated L- or D-1,2-glucals starting from the corresponding alpha- or beta-glycopyranosylethanals is described. The key step of the approach is the stereoselective cycloaddition of chiral vinyl ethers derived from both enantiomers of mandelic acid. The preparation of 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-L-arabino-hex-1-enitol, 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-D-arabino-hex-1-enitol, and 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)methyl]-D-arabino-hex-1-enitol serves as an example of this approach.
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