Novel efficient routes to heparin monosaccharides and disaccharides achieved via regio- and stereoselective glycosidation.
A new methodology for the synthesis of heparin building blocks has been developed. We describe novel efficient routes to both L-iduronic acid and D-glucuronic acid acceptors. Glycosylation with thioglycosides donors gave corresponding disaccharides in a regio- and stereoselective fashion. An improved approach to synthesizing azido-glucose thioglycoside donor to render azido-sugar from mannose via nucleophilic substitution is described. [reaction: see text]
Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Henry N
HN
Yu
Jun-ichi
J
Furukawa
Tsuyoshi
T
Ikeda
Chi-Huey
CH
Wong
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006493:Heparin / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004187:Disaccharides; D009005:Monosaccharides; D006493:Heparin