NUCLEIC-ACID RELATED-COMPOUNDS .77. 2',3'-DIDEHYDRO-2',3'-DIDEOXY-2'(AND 3')-METHYLNUCLEOSIDES VIA [3,3]-SIGMATROPIC REARRANGEMENTS OF 2'(AND 3')-METHYLENE-3'(AND 2')-O-THIOCARBONYL DERIVATIVES AND RADICAL REDUCTION OF A 2'-CHLORO-3'-METHYLENE ANALOG

被引：9

作者：

SAMANO, V ^{[1
]}

ROBINS, MJ ^{[1
]}

机构：

[1] BRIGHAM YOUNG UNIV,DEPT CHEM,PROVO,UT 84602

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1993年 / 71卷 / 02期

关键词：

D O I：

10.1139/v93-027

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of 5'-O-(tert-butyldiphenylsilyl)-2'(and 3')-deoxy-2'(and 3')-methyleneuridine (and adenosine) derivatives with phenyl chlorothionocarbonate gave the 3'(and 2')-O-phenoxythiocarbonyl intermediates, which underwent spontaneous [3,31-sigmatropic rearrangement to give the 2',3'-didehydro-2',3'-dideoxy-2'(and 3')-(phenoxycarbonylthio)methyl analogues. These allylic thioesters were subjected to tributylstannane-mediated hydrodesulfurization and deprotection to give 2',3'-didehydro-2',3'-dideoxy-2'(and 3')-methyluridine (and adenosine). Tributylstannane-mediated hydrodehalogenation of a 2'-chloro-2',3'-dideoxy-3'-methyleneuridine derivative afforded the 2',3'-didehydro-2',3'-dideoxy-3'-methyl product of allylic transposition exclusively.

引用

页码：186 / 191

页数：6

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