SYNTHESIS OF MESO-2',3'-DIDEOXY-3'BETA-HYDROXYMETHYL CARBOCYCLIC NUCLEOSIDES AS POTENTIAL ANTIVIRAL DRUGS - UNUSUAL COMPETITIVE 2-O-VERSUS N-1-ALKYLATION OF 3-SUBSTITUTED PYRIMIDINES UNDER MITSUNOBU CONDITIONS

被引:27
作者
BONNAL, C [1 ]
CHAVIS, C [1 ]
LUCAS, M [1 ]
机构
[1] UNIV MONTPELLIER 2,CHIM BIOORGAN LAB,F-34095 MONTPELLIER 5,FRANCE
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 11期
关键词
D O I
10.1039/p19940001401
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of meso-2',3'-dideoxy-3'beta-hydroxymethyl carbocyclic nucleosides as potential antiviral drugs via the alkylation of protected purines and pyrimidines with meso-beta,beta'-disubstituted cyclopentanols under Mitsunobu conditions is described. Chemical evidence for an unusual competitive 2-O vs. N-1-alkylation of 3-substituted pyrimidines is presented.
引用
收藏
页码:1401 / 1410
页数:10
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