RADICAL REARRANGEMENT OF 2-O-(DIPHENYLPHOSPHORYL)GLYCOSYL BROMIDES - A NEW SYNTHESIS FOR 2-DEOXY DISACCHARIDES AND 2-DEOXY RIBONUCLEOSIDES

被引：60

作者：

KOCH, A

LAMBERTH, C

WETTERICH, F

GIESE, B

机构：

[1] UNIV BASEL,DEPT CHEM,ST JOHANNS-RING 19,CH-4056 BASEL,SWITZERLAND

[2] TH DARMSTADT,INST ORGAN CHEM,W-6100 DARMSTADT,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 05期

关键词：

D O I：

10.1021/jo00057a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Deoxy-1-O-diphenylphosphoryl glycosides react with nucleophiles under mild conditions giving access to 2-deoxy disaccharides and nucleosides. The intermediate 2-deoxy-1-O-diphenylphosphoryl compounds were generated in situ by a radical 2 --> 1 migration of the phosphate ester group. This is the first observation of a rearrangement of a phosphate ester in radicals. ESR experiments and quenching of the radical at C2 by tin hydride or tin deuteride were used to detect the intermediates and to prove their structure.

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页码：1083 / 1089

页数：7

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