Synthesis and Property Studies of Naphth [1,2-d]imidazole Ribonucleosides PDF

Keywords

Anomeric mixture, nucleosides, imidazole, chromatography

Abstract

The fusion reaction between 1-Trimethylsilylnaphth[1,2-d]imidazole 9 and 2,3.5-Tri-O-benzoyl-1-bromo-D- ribofuranose 11 lead to an anomeric mixture of 2', 3', 5' -Tri-O benzoyl-1-alpha-D-ribofuranosylnaphth[1.2-d]imidazole 12 and 2',3', 5' -Tri-O-benzoyl-1-beta-D-ribofuranosylnaphth[1.2-d]imidazole 14. The previous anomeric mixture was also prepared with another method i.e., by treating 1 Trimethylsilylnaphth[1,2-d]imidazole 9 with 1-O-acetyl 2,3,5-Tri-O-benzoyl-beta-D-ribofuranose 10 in the presence of Triflate. Separation of the anomers was achieved by chromatographical means and debenzoylation yielded the corresponding nucleosides 13 and 15. Structural proofs are based on elemental analysis, UV, 1H and 13 CNMR