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Syntheses of a branched heptasaccharide having phytoalexin-elicitor activity

✍ Scribed by Peter Fügedi; Winnie Birberg; Per J. Garegg; Åke Pilotti

Book ID
102992334
Publisher
Elsevier Science
Year
1987
Tongue
English
Weight
995 KB
Volume
164
Category
Article
ISSN
0008-6215

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✦ Synopsis

Syntheses are described of a D-glucose heptasaccharide, 1, corresponding to a glucan structure recognised by the soybean when infected by the fungus Phytophthora megasperma f. sp. giycineu and which stimulates the formation of phytoalexins. The synthetic strategy is based upon l,Ztrans-glycoside formation assisted by participating benzoate groups in the 2-position, with silver triflate as promoter and glycosyl bromides as donors for making the smaller fragments, and with methyl triflate as promoter with thioglycosides as donors for making the larger ones. Regioselective reductive openings of 4,6-benzylidene acetals play a key role in obtaining free 6-OH groups with benzyl protection at O-4.

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A further reaction, involving the sodium salt of the peracetylated β-isomeric pentathiohexa-and hexathioheptasaccharides 12,34 and 28,39, respectively, were all found to be active in 1-thio derivative of 12 with 1,2,3,4-tetra-O-acetyl-6-deoxy-6iodo-β-D-glucopyranose ( 26), afforded the homologous el