Beta-selective arabinofuranosylation using a 2,3-O-xylylene-protected donor.
Reported is a novel stereoselective beta-arabinofuranosylation that makes use of a conformationally restricted 2,3-O-xylylene-protected arabinofuranosyl donor. Optimization of the reaction conditions showed that factors including the structure of the acceptor alcohol, substrate concentration, and protecting group on O-5 of the donor affect the stereochemical outcome of the glycosylation. To demonstrate the utility of the methodology, the synthesis of an oligosaccharide fragment from the mycobacterial cell wall polysaccharide lipoarabinomannan was carried out.
Imamura
Akihiro
A
Alberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, The University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, Alberta T6G 2G2, Canada.
Lowary
Todd L
TL
D020650:Combinatorial Chemistry Techniques; D006031:Glycosylation; D008070:Lipopolysaccharides / Q000737:chemistry*; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009161:Mycobacterium / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014992:Xylenes / Q000737:chemistry
D008070:Lipopolysaccharides; D009844:Oligosaccharides; D014992:Xylenes; C050016:lipoarabinomannan; D008358:Mannose