Glycosylation Using Hemiacetal Sugar Derivatives: Synthesis of O-α-d-Rhamnosyl-(1→3)-O-α-d-rhamnosyl-(1→2)-d-rhamnose and O-α-d-Tyvelosyl-(1→3)-O-α-d-mannosyl-(1→4)-l-rhamnose
- 1 July 2003
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 76 (7) , 1409-1421
- https://doi.org/10.1246/bcsj.76.1409
Abstract
O-α-d-Rhamnopyranosyl-(1→3)-O-α-d-rhamnopyranosyl-(1→2)-d-rhamnopyranose, a repeating trisaccharide of the O-specific polysaccharides (OPSs) of Pseudomonades, and O-α-d-tyvelopyranosyl-(1→3)-O-α-d-mannopyranosyl-(1→4)-l-rhamnopyranose, a trisaccharide composing the OPSs of Salmonella typhi, were synthesized by in-situ activating glycosylation reactions using hemiacetal sugar derivatives. Allyl 2,4-di-O-benzyl-α-d-rhamnopyranoside was prepared via the direct ditritylation of allyl α-d-mannopyranoside. 3-O-Acetyl-2,4-di-O-benzyl-d-rhamnopyranose was used as a precursor for the moiety of d-tyvelose (3,6-dideoxy-d-arabino-hexose, 3,6-dideoxy-d-mannopyranose, 3-deoxy-d-rhamnose) of the salmonella trisaccharide.This publication has 77 references indexed in Scilit:
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