The allyl group for protection in carbohydrate chemistry. 17. Synthesis of propyl O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3- di-O-methyl-alpha-L-rhamnopyranosyl)-(1----2)-3-O-methyl-alpha- L-rhamnopyranoside: the oligosaccharide portion of the major serologically active glycolipid from Mycobacterium leprae.
Allyl 4-O-benzyl-alpha-L-rhamnopyranoside was converted into allyl 4-O-benzyl-3-O-methyl-alpha-L-rhamnopyranoside and this was condensed with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl chloride to give a disaccharide derivative which was converted into allyl 4-O-benzyl-2-O-(2,3-O-isopropylidene-alpha-L-rhamnopyranosyl)-3-O-methyl -alpha- L-rhamnopyranoside. This disaccharide derivative was condensed with 2,4-di-O-acetyl-3,6-di-O-methyl-alpha-D-glucopyranosyl chloride to give a trisaccharide derivative which was converted into the title compound. This compound represents the oligosaccharide portion of the major serologically active glycolipid from Mycobacterium leprae which is required to prepare a synthetic diagnostic agent for leprosy infection at an early stage and to investigate the specificities of monoclonal antibodies directed towards the glycolipid.
D006017:Glycolipids / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009166:Mycobacterium leprae / Q000276:immunology*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D009904:Optical Rotation; D014312:Trisaccharides / Q000138:chemical synthesis*
D006017:Glycolipids; D007202:Indicators and Reagents; D009844:Oligosaccharides; D014312:Trisaccharides; C047673:propyl O-(3,6-di-O-methyl-beta-glucopyranosyl)-(1-4)-O-(2,3-di-O-methyl-alpha-rhamnopyranosyl)-(1-2)-3-O-methyl-alpha-rhamnopyranoside