Mild synthesis of disaccharidic 2,3-enopyranosyl cyanides and 2-C-2-deoxy pyranosyl cyanides with Hg(CN)2/HgBr2/TMSCN

被引：18

作者：

Franz, AH ^{[1
]}

Wei, YQ ^{[1
]}

Samoshin, VV ^{[1
]}

Gross, PH ^{[1
]}

机构：

[1] Univ Pacific, Dept Chem, Stockton, CA 95211 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 22期

关键词：

D O I：

10.1021/jo0111661

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid-catalyzed dimerization of mono- and disaccharidic per-O-acetylated glycals gave di- and tetrasaccharidic O-acetylated C-glycosides, respectively. 2,3-Enopyranosyl cyanides were obtained from per-O-acetylated glycals by a new, mild anomeric S-N'-acetoxy displacement with Hg(CN)(2)/HgBr2/TMSCN. Per-O-acetylated 2-C-2-deoxy-pyranoses were converted into pyranosyl cyanides by the same reagent. An unprecedented acetic acid elimination from dimers with D-galacto- and L-fuco-configurations accompanied the S-N-displacement under those conditions. A new set of H-1 NMR coupling constants for 2,3-enopyranosyl systems was used for configurational assignment of complicated tetrasaccharide mimics.

引用

页码：7662 / 7669

页数：8

共 34 条

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[Anonymous], CARBOHYDRATES

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