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Synthesis 2009(2): 199-204  
DOI: 10.1055/s-0028-1083292
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Synthesis of an Allose-Containing Analogue of the Phytoalexin-Elicitor Glucohexaose and Its Dodecyl Glycoside

Hongju Ma, Dewen Qiu, Xiangdong Mei*, Jun Ning*, Qianfei Zhao, Yonghong Li
State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, P. R. of China
Fax: +86(10)62899142; e-Mail: meixiangdong@gmail.com; e-Mail: jning@ippcaas.cn;
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Publication History

Received 28 July 2008
Publication Date:
19 December 2008 (online)

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Abstract

An allose-containing analogue 2 of the phytoalexin elicitor β-(1→3)-branched β-(1→6)-linked glucohexatose and its dodecyl glycoside 3 has been regio- and stereospecifically synthesized. As a typical example of the method, the synthesis of 2 was achieved via coupling of the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-β-d-glucopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-β-d-glucopyranosyl-(1→6)]-1,2-O-isopropylidene-α-d-allopyranosyl trichloroacetimidate (9) with a trisaccharide acceptor. The donor was prepared easily from 1,2:5,6-di-O-isopropylidene-α-d-allofuranose (5) and 2,3,4,6-tetra-O-benzoyl-α-d-glucopyranosyl trichloroacetimidate (4) in a regio- and stereoselective manner.

Key words

oligosaccharides - synthesis - glycosides - glycosylations - stereoselectivity