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

Yuetao Yi; Zhongxuan Zhou; Jun Ning; Fanzuo Kong; Jianqiang Li

doi:10.1055/s-2003-37644

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

Yuetao Yi^a, Zhongxuan Zhou^a, Jun Ning*^a, Fanzuo Kong^a, Jianqiang Li^b
^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;

Abstract

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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

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

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