The allyl group for protection in carbohydrate chemistry. 17. Synthesis of propyl O-(3,6-di-O-methyl-β-D-glucopyranosyl)- (1→4)-O-(2,3-di-O-methyl-α-L-rhamnopyranosyl)-(1 → 2)-3-O-methyl-α-L-rhamnopyranoside: the oligosaccharide portion of the major serologically active glycolipid from Mycobacterium leprae
✍ Scribed by Jill Gigg; Roy Gigg; Sheila Payne; Robert Conant
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- English
- Weight
- 474 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
Allyl 4-O-benzyl-~-L-rhamnopyranoside was converted into allyl 4-O-benzyl-3-O-methyl-oeL-rhamnopyranoside and this was condensed with 2,3,4-tri-O-acetyl-~-L-rhamnopyranosyl chloride to give a disaccharide derivative which was converted into allyl 4
This disaccharide derivative was condensed with 2,4-di-O-aeetyl-3,6-di-O-methyl-~-D-glucopyranosyl chloride to give a trisaceharide derivative which was converted into the title compound. This compound represents the oligosaccharide portion of the major serologicaliy active glyeolipid 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.