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

Authors
SAKTHIVEL K KUMAR RK PATHAK T
Citation
K. Sakthivel et al., REACTIONS OF DIMESYLTHYMIDINE WITH SECONDARY-AMINES - EASY ACCESS TO ,5'-DIDEOXY-3'-SUBSTITUTED-5'-ALKYLAMINOTHYMIDINES - NEW CLASSES OF POTENTIAL ANTIVIRAL AMINONUCLEOSIDES, Tetrahedron, 49(20), 1993, pp. 4365-4372
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
20
Year of publication
1993
Pages
4365 - 4372
Database
ISI
SICI code
0040-4020(1993)49:20<4365:RODWS->2.0.ZU;2-Y
Abstract
3,5'-Di-O-mesylthymidine 4a (DMST) on reaction with secondary amines u ndergoes hitherto unknown ''one-pot-two-steps'' transformation to prod uce 2,3'-O-anhydro-5'-deoxy-5'-alkylaminothymidines 5a-h. Most of the amines used, irrespective of their basicities showed remarkable select ivity towards the 5'-substitution over the 2,3'-O-anhydro ring formati on. Compounds 5a-h could be used as intermediates for the synthesis of a variety of ,5'-dideoxy-3'-substituted-5'-alkylaminothymidines of th e type 9, 10a-b, 11.