V. Nair, B. J. Hettrick
1988
Citations
0
Influential Citations
8
Citations
Journal
Tetrahedron
Abstract
Abstract 2-Methylsulfonylnebularine has been synthesized from 2-aminonebularine (lsoadenosine or 2-aminopurine ribonucleoside) by a radical deamination-thioalkylation followed by sulfur oxidation. This sulfone is potentially an intermediate for the synthesis of many new 2-substituted analogues of nebularine as the nucleofugic methylsulfonyl group can be displaced by a variety of nucleophiles. Representative examples Include 2-cyano-, 2-carboxamido-, 2-acetamido-, and 2-bis (carboxamido)methyl- nebularine. Structures of the intermediate and products were confirmed by spectroscopic data, particularly high-field NMR and FAB HRMS data.