3,4-Dipyranosyl-1,2,5-oxadiazole 2-oxides: synthesis and X-ray structure

被引：19

作者：

Baker, KWJ ^{[1
]}

March, AR ^{[1
]}

Parsons, S ^{[1
]}

Paton, RM ^{[1
]}

Stewart, GW ^{[1
]}

机构：

[1] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

TETRAHEDRON | 2002年 / 58卷 / 42期

基金：

英国工程与自然科学研究理事会;

关键词：

nitrile oxides; C-glycosides; pyranosylcarbaldoximes; pyranosylnitromethanes; X-ray crystallography;

D O I：

10.1016/S0040-4020(02)01023-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,4-Di(2,3,4,6-tetra-O-acetyl-beta-D-mannopyranosyl)-1,2,5-oxadiazole 2-oxide (7) has been synthesised from D-mannose by a route involving as the key stop dimerisation of mannopyranosyl nitrile oxide 2. Three methods were used for the generation of the nitrile oxide: isocyanate-mediated dehydration of nitromethylmannose derivative 4, treatment of aldoxime 5 with aq. hypochlorite, and base-induced dehydrochlorination of hydroximoyl chloride 6. D-Gluco, D-galacto, D-xylo, and L-fucopyranosyl analogues 8-11 were prepared similarly. The structure of D-mannose-derived 1,2,5-oxadiazole 2-oxide 7 was established by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8505 / 8513

页数：9

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