Synthesis and stereoselective glycosylation of D- and L-glycero-beta-D-manno-heptopyranoses.
[reaction: see text] A method for the direct stereocontrolled synthesis of D- and L-glycero-beta-D-manno-heptopyranosides such as those found in the repeating unit of the O-specific polysaccharide from the CNCTC 113/92 LPS (serotype 54) is described. The method relies on the presence of a 4,6-O-benzylidene acetal to effect stereocontrol at the anomeric center; the configuration at C6 (L- or D-glycero) is of minimal importance.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Banerjee
Abhisek
A
D002240:Carbohydrate Sequence; D006031:Glycosylation; D006539:Heptoses / Q000138:chemical synthesis*; D008070:Lipopolysaccharides / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D016981:Plesiomonas / Q000737:chemistry*; D013237:Stereoisomerism
D006539:Heptoses; D008070:Lipopolysaccharides