The total synthesis of C-glycosides with completely resolved seven-carbon backbone polyol stereochemistry: Stereochemical correlations and access to L-configured and other rare carbohydrates

被引：0

作者：

Hoffmann, HMR ^{[1
]}

Dunkel, R ^{[1
]}

Mentzel, M ^{[1
]}

Reuter, H ^{[1
]}

Stark, CBW ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Dept Organ Chem, D-30167 Hannover, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2001年 / 7卷 / 22期

关键词：

carbohydrates; C-glycosides; cycloaddition; de novo syntheses; stereochemical coalescence;

D O I：

10.1002/1521-3765(20011119)7:22<4771::AID-CHEM4771>3.3.CO;2-A

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The de novo synthesis of a full set of hydroxymethyl C-glycosides from only two precursors is described. The seven-carbon target molecules contain five stereocentres and bridge the stereochemical gap between natural D-configured and non-natural L-configured series of hexoses. Key steps include hydroxylation. differential protection, stereoselective reduction and desymmetrization of 8-oxabicyclo[3.2.1]oct-6-enes. C-Terminus differentiation and C-terminus excision of the seven-carbon polyol backbone lead to hexoses. including those of the L-series. A stereochemical and genetic classification of C-glycosides is presented.

引用

页码：4771 / 4789

页数：19