title: 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.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi , Delhi 110 007, India.
authors.forename: Vinod
authors.initials: V
authors.lastname: Khatri
authors.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi , Delhi 110 007, India.
authors.forename: Amit
authors.initials: A
authors.lastname: Kumar
authors.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi , Delhi 110 007, India.
authors.forename: Balram
authors.initials: B
authors.lastname: Singh
authors.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi , Delhi 110 007, India.
authors.forename: Shashwat
authors.initials: S
authors.lastname: Malhotra
authors.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi , Delhi 110 007, India.
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Prasad
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry*; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000737:chemistry*
chemical_list: C000606353:1-phenyl-2-(2',3',4',6'-tetra-O-acetyl-beta-D-glycopyranosyl)ethanone; D000447:Aldehydes; D006027:Glycosides; D009005:Monosaccharides; D013402:Sugar Alcohols; D008358:Mannose; D005690:Galactose