Synthesis of di-O-glycosyl derivatives of methyl α-l-rhamnopyranoside☆

Add time:09/26/2019    Source:sciencedirect.com

The syntheses are described of 2,3-di-O-glycosyl derivatives (1–12) of methyl α-l-rhamnopyranoside where the glycosyl moieties are variously α-l-fucopyranose, β-l-fucopyranose, β-d-glucopyranose, α-d-mannopyranose. The syntheses involve stereoselective glycosylation of methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-α-l-rhamnopyranosyl)-α-l-rhamnopyranoside (21), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-α-d-mannopyranosyl)-α-l-rhamnopyranoside (25), methyl 4-O-benzoyl-O-(2,3,4,6-tetra-O-benzoyl-β-d-glucopyranoside (29), methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-β-l-fucopyranosyl)-α-l-rhamnopyranoside (35), and methyl 4-O-benzyl-2-O-(2,3,4-tri-O-benzoyl-β-l-fucopyranosyl)-α-l-rhamnopyranoside (59). In the syntheses of compounds 7–9, the α-l-fucopyranosyl residues are introduced stereoselectively, using 2,3,4-tri-O-benzoyl-α-l-fucopyranosyl bromide (17) and ethyl 2,3,4-tri-O-acetyl-1-thio-β-l-fucopyranoside (47) as glycosyl donors.

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