Synthesis of α-Arabinose Nucleosides from 6-Substituted Uracils

✍ Scribed by Jørgensen, Per T. ;El-Barbary, Ahmed A. ;Pedersen, Erik B.

• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: English
• Weight: 517 KB
• Volume: 1993
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199319930102

✦ Synopsis

Abstract

The reaction of silylated 6‐substituted uracils 5 with methyl 2,3,5‐tri‐O‐benzoyl‐α‐D‐arabinofuranoside (3) in the presence of trimethylsilyl trifluoromethanesulfonate (TMS triflate) afforded a mixture of the corresponding protected N^1^,N^3^‐bis(arabinofuranosyl)uracils 6 and the 6‐substituted 2,3,5‐tri‐O‐benzoyl‐α‐D‐arabinofuranosyluracils 8. Deprotection of 6 and 8 gave the corresponding α nucleosides 7 and 9. The reaction of silylated 6‐ethyl‐ and 6‐methylthiouracil with 3 afforded a mixture of S‐ and N^3^‐glycosides 10 and 11. The glycosides 10 were deblocked by treatment with methanolic ammonia to obtain the deprotected α nucleosides 12.