Issue 8, 2008
From the journal:

Organic & Biomolecular Chemistry

Stereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside†

Sang-Hyun Son,a   Chiharu Tano,a   Jun-ichi Furukawa,a   Tetsuya Furuikea  and  Nobuo Sakairi*a  

* Corresponding authors

a Division of Environment Materials Science, Graduate School of Environmental Science, Hokkaido University, Kita-ku, Sapporo 060-0810, Japan
E-mail: saka@ees.hokudai.ac.jp
Fax: +81-11-706-2257
Tel: +81-11-706-2257

Abstract

Dodecyl thioglycosides (3, 4, 5) were prepared by conventional transformation of D-glucose and used as new glycosyl donors for a short-step synthesis of phytoalexin elicitor heptaglucoside. A gentio-tetraoside derivative (6) having three hydroxyl groups was synthesized by NIS–TfOH promoted glycosylate in more than 90% yield followed by selective removal of temporary protective groups. Undesired formation of α-glycosides at the introduction of β-(1→3)-branches into gentio-oligosaccharides was found to be suppressed by use of a thiophilic reagent system, BSP (1-benzenesulfinyl piperidine)–Tf2O, giving the heptaglucoside in only four glycosylation steps.

Graphical abstract: Stereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside

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Article information

DOI
https://doi.org/10.1039/B800809D
Article type
Paper
Submitted
16 Jan 2008
Accepted
25 Jan 2008
First published
22 Feb 2008

Org. Biomol. Chem., 2008,6, 1441-1449

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Stereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside

S. Son, C. Tano, J. Furukawa, T. Furuike and N. Sakairi, Org. Biomol. Chem., 2008, 6, 1441 DOI: 10.1039/B800809D

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