A general strategy for the synthesis of 3,6-branched gluco-oligosaccharides: facile synthesis of the phytoalexin elicitor oligosaccharides

A general method for the synthesis of 3,6-branched gluco-oligosaccharides has been developed. As a typical example of the method, the synthesis of the glucohexatose phytoalexin elicitor on a large scale was achieved via coupling of a trisaccharide donor with a trisaccharide acceptor. The donor and a...

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Bibliographic Details
Published in:Tetrahedron letters 2002-08, Vol.43 (32), p.5545-5549
Main Authors: Ning, Jun, Yi, Yuetao, Kong, Fanzuo
Format: Article
Language:English
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Summary:A general method for the synthesis of 3,6-branched gluco-oligosaccharides has been developed. As a typical example of the method, the synthesis of the glucohexatose phytoalexin elicitor on a large scale was achieved via coupling of a trisaccharide donor with a trisaccharide acceptor. The donor and acceptor were prepared easily from 1,2:5,6-di- O-isopropylidene-α- d-glucofuranose, 2,3,4,6-tetra- O-benzoyl-α- d-glucopyranosyl trichloroacetimidate, and 6- O-acetyl-2,3,4-tri- O-benzoyl-α- d-glucopyranosyl trichloroacetimidate in a regio- and stereoselective manner. Higher oligosaccharides of the elicitor including the hepta-, nona-, dodeca- and tetradecasaccharides have also been readily synthesized by this strategy. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01143-7