C6 substitution of inosine using hexamethylphosphorous triamide in conjunction with carbon tetrahalide or N-halosuccinimide

✍ Scribed by Eduardo A Véliz; Peter A Beal

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 83 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00051-4

✦ Synopsis

Herein we report the facile conversion of 2 ,3 ,5 -tri-O-acetylinosine to three different nucleoside analogs via reaction of hexamethylphosphorous triamide and an organic halide. Acetyl-protected 6-bromopurine riboside, 6-chloropurine riboside and N 6 ,N 6 -dimethyladenosine can each be prepared in good yield from 2 ,3 ,5 -tri-Oacetylinosine, HMPT and halide. The major product of the reaction is determined by the identity of the halide used and the reaction temperature.