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  • Title: Synthesis of di-O-glycosyl derivatives of methyl alpha-L-rhamnopyranoside.
    Author: Nifant'ev NE, Lipkind GM, Shashkov AS, Kochetkov NK.
    Journal: Carbohydr Res; 1992 Jan; 223():109-28. PubMed ID: 1596912.
    Abstract:
    The syntheses are described of 2,3-di-O-glycosyl derivatives (1-12) of methyl alpha-L-rhamnopyranoside where the glycosyl moieties are variously alpha-L-fucopyranose, beta-L-fucopyranose, beta-D-glucopyranose, alpha-D-mannopyranose, and alpha-L-rhamnopyranose. The syntheses involve stereoselective glycosylation of methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-alpha-L- rhamnopyranosyl)-alpha-L-rhamnopyranoside (21), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl)- alpha-L-rhamnopyranoside (25), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl)- alpha-L-rhamnopyranoside (29), methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-beta-L-fucopyranosyl)-alpha-L- rhamnopyranoside (35), and methyl 4-O-benzyl-2-O-(2,3,4-tri-O-benzoyl-beta-L-fucopyranosyl)- alpha-L-rhamnopyranoside (59). In the syntheses of compounds 7-9, the alpha-L-fucopyranosyl residues are introduced stereoselectively, using 2,3,4-tri-O-benzoyl-alpha-L-fucopyranosyl bromide (17) and ethyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside (47) as glycosyl donors.
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