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
收藏
页码：186 / 191
页数：6
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