Synthesis of β-C-Glycopyranosyl Aldehydes and 2,6-Anhydro-heptitols.

Abstract

A convenient route has been developed for the diastereoselective synthesis of β-C-glycopyranosyl aldehydes from D-glucose, D-mannose, and D-galactose. The key step in the synthesis of C-glycosyl aldehydes is the aryl driven reductive dehydration on 1-phenyl-2-(2',3',4',6'-tetra-O-acetyl-β-D-glycopyranosyl)ethanone to afford alkenes, which on oxidation afford the desired compounds in good yield. β-C-Glycopyranosyl aldehydes have been converted to 2,6-anhydro-heptitols in quantitative yields. The 2,6-anhydro-heptitols derived from D-mannose and D-galactose are enantiomeric and are useful linkers for the synthesis of macrocycles/amphiphiles of complementary chirality.

• Authors: Vinod Khatri, Amit Kumar, Balram Singh, Shashwat Malhotra, Ashok K Prasad
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 80 Issue 21 Pg. 11169-74 (Nov 06 2015) ISSN: 1520-6904 [Electronic] United States
• PMID: 26421380 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 1-phenyl-2-(2',3',4',6'-tetra-O-acetyl-beta-D-glycopyranosyl)ethanone
• Aldehydes
• Glycosides
• Monosaccharides
• Sugar Alcohols
• Mannose
• Galactose

Topics

• Aldehydes (chemical synthesis, chemistry)
• Galactose (chemistry)
• Glycosides (chemical synthesis, chemistry)
• Magnetic Resonance Spectroscopy
• Mannose (chemistry)
• Monosaccharides (chemistry)
• Stereoisomerism
• Sugar Alcohols (chemistry)