Nucleic acid related compounds. 66. Improved syntheses of 5'-chloro-5'-deoxy-and 5'-S-aryl (or alkyl)-5'-thionucleosides

MJ Robins, F Hansske, SF Wnuk…

Index: Robins; Hansske; Wnuk; Kanai Canadian Journal of Chemistry, 1991 , vol. 69, # 9 p. 1468 - 1474

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Citation Number: 62

Abstract

Treatment of ribonucleosides with thionyl chloride/pyridine/acetonitrile (0° 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 ...