Polymer-supported solution synthesis of a heptaglucoside having phytoalexin elicitor activity
β Scribed by R. Verduyn; P. A. M. van der Klein; M. Douwes; G. A. van der Marel; J. H. van Boom
- Book ID
- 104589550
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 232 KB
- Volume
- 112
- Category
- Article
- ISSN
- 0165-0513
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β¦ Synopsis
Abstract
An efficient synthesis of methyl heptaglucoside 2 using poly(ethyleneglycol)monomethyl ether as a polymer support is described. Elongation of the acceptor 11, anchored via a succinoyl linkage to PEG, with the appropriate glycosyl donors 4β6 and intermittent protective group manipulations gave fully protected heptamer 18. Deprotection of 18 furnished, after purification as its peracetate, title compound 2 in a good overall yield.
π SIMILAR VOLUMES
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 for
We describe a highly convergent approach for the synthesis of the tetraglucosyl glucitol 1 and its derivatives 4, 5 and 6 which exhibit phytoalexin-elicitor activity in rice cells based on sequential glycosylation.
A diverse library of 2-aminobenzoxazines 3 has been synthesized using a two step approach. Addition of anthnmilie acids to isoeyanates affords ureas 2 that can be eyelized by polymer-supported EDC to give 2-aminobenzoxazines 3.