NUCLEIC-ACID RELATED-COMPOUNDS .66. IMPROVED SYNTHESES OF 5'-CHLORO-5'-DEOXYNUCLEOSIDES AND 5'-S-ARYL(OR ALKYL)-5'-THIONUCLEOSIDES

被引：46

作者：

ROBINS, MJ ^{[1
]}

HANSSKE, F ^{[1
]}

WNUK, SF ^{[1
]}

KANAI, T ^{[1
]}

机构：

[1] UNIV ALBERTA,DEPT CHEM,EDMONTON T6G 2G2,ALBERTA,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1991年 / 69卷 / 09期

关键词：

ADENOSINE; 5'-S-ARYL(OR ALKYL)-5'-THIONUCLEOSIDES; 5'-CHLORO-5'-DEOXYNUCLEOSIDES; URIDINE; NUCLEOSIDES;

D O I：

10.1139/v91-217

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of ribonucleosides with thionyl chloride/pyridine/acetonitrile (0-degrees-C to ambient temperature) resulted in essentially quantitative formation of 5'-chloro-5'-deoxy-2',3'-O-sulfinylnucleoside derivatives. These diastereomeric sulfite esters underwent deprotection readily with aqueous methanolic ammonia. This gave 5'-chloro-5'-deoxynucleosides without use of the suspected carcinogen, hexamethylphosphoramide (HMPA). Nucleophilic displacement with sodium thiolates in dimethylformamide (-30-degrees-C to ambient temperature) gave 5'-S-aryl(or alkyl)-5'-thionucleosides in high yields. Treatment of ribonucleosides wit thionyl chloride/acetonitrile without pyridine followed by aqueous work-up gave diastereomeric 2',3'-O-sulfinylnucleosides with an unmodified 5'-hydroxyl group. Diagnostic NMR shifts for cyclic sulfite ester stereochemistry are noted.

引用

页码：1468 / 1474

页数：7

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