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Synthesis of β-(1 → 6)-Branched (1 → 3)-Glucononaoside with Alternate β-and α-Bonds in the Backbone

✍ Scribed by Zi-Cheng Wu; Jun Ning; Fan-Zuo Kong

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
546 KB
Volume
21
Category
Article
ISSN
0256-7660

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✦ Synopsis

Abstract

Lauryl glycoside of β‐D‐Gic__p__‐(1 → 3)‐[β‐D‐Glc__p__‐(1 → 6)‐] a‐D‐Glc__p__‐(1 → 3)‐β‐D‐Glc__p__‐(1 → 3)‐[β‐D‐Glc__p__‐(1 → 6)‐] a‐D‐Glc__p__‐(1 → 3)‐β‐D‐Glc__p__‐(1 → 3)‐[β‐D‐Glc__p__‐(1 → 6)‐]β‐D‐Glc__p__ was synthesized through 3 + 3 + 3 strategy. 3‐O‐Allyl‐2, 4, 6‐tri‐O‐benzoyl‐β‐D‐glucopyranosyl‐(1 → 3)‐[2, 3, 4, 6‐tetra‐O‐benzoyl‐β‐D‐glucopyranosyl‐(1 → 6)‐] 1, 2‐O‐isopropylidene‐a‐D‐glucofuranose was used as the key intermediate which was converted to the corresponding trisaccharide donor and acceptor readily.

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The branched, sulfur-linked tetrasaccharide S-(beta-D-glucopyranosyl)-(1-->3)-S-[(6-S-beta-D-glucopyranosyl)-3,6-dit hio- beta-D-glucopyranosyl]-(1-->3)-S-3-thio-D-glucopyranose (9) has been conveniently prepared by SN2 displacement of the triflate group in 1,2:5,6-di-O-isopropylidene-3-O-trifluorom