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Synthesis 2003(4): 0491-0496
DOI: 10.1055/s-2003-37644
PAPER
© Georg Thieme Verlag Stuttgart · New York

Highly Efficient Syntheses of the Phytoalexin-Elicitor Active β-(1→3)-Branched­ β-(1→6)-Linked Heptaglucose and Its Dodecyl Glycoside

Yuetao Yia, Zhongxuan Zhoua, Jun Ning*a, Fanzuo Konga, Jianqiang Lib
a Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, P. O. Box 2871, Beijing 100085, China
b Department of Plant Pathology, China Agricultural University, Beijing 100094, China
Fax: +86(10)62923563; e-Mail: jning@mail.rcees.ac.cn;
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Publication History

Received 31 October 2002
Publication Date:
07 March 2003 (online)

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Abstract

A highly efficient method for the synthesis of 3,6-branched gluco-oligosaccharides was developed by using 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 through a regio- and stereoselective manner. The β-(1→3)-branched β-(1→6)-linked heptaglucose 1 and its dodecyl glycoside 2 having phytoalexin-elicitor activity were prepared using the developed strategy. Bioassays showed that the phytoalexin-elicitor activity of the do­decyl β-(1→3)-branched β-(1→6)-linked hexaglucoside 2 is slightly more than that of the corresponding reducing end free heptaglucose 1.

Key words

oligosaccharides - phytoalexin-elicitor - synthesis - glycosides - glycosylations