REACTIONS OF DIMESYLTHYMIDINE WITH SECONDARY-AMINES - EASY ACCESS TO 3',5'-DIDEOXY-3'-SUBSTITUTED-5'-ALKYLAMINOTHYMIDINES - NEW CLASSES OF POTENTIAL ANTIVIRAL AMINONUCLEOSIDES

被引:12
作者
SAKTHIVEL, K [1 ]
KUMAR, RK [1 ]
PATHAK, T [1 ]
机构
[1] NATL CHEM LAB,ORGAN CHEM DIV SYNTH,BIOORGAN CHEM UNIT,POONA 411008,MAHARASHTRA,INDIA
关键词
D O I
10.1016/S0040-4020(01)85753-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3,5'-Di-O-mesylthymidine 4a (DMST) on reaction with secondary amines undergoes hitherto unknown ''one-pot-two-steps'' transformation to produce 2,3'-O-anhydro-5'-deoxy-5'-alkylaminothymidines 5a-h. Most of the amines used, irrespective of their basicities showed remarkable selectivity towards the 5'-substitution over the 2,3'-O-anhydro ring formation. Compounds 5a-h could be used as intermediates for the synthesis of a variety of 3,5'-dideoxy-3'-substituted-5'-alkylaminothymidines of the type 9, 10a-b, 11.
引用
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页码:4365 / 4372
页数:8
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