186648-81-7

Upstream product

• 16205-60-0 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 142822-37-5 4-{(1S,2S)-3-Azido-2-chloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1H-imidazole 
• 142822-36-4 4-{(1S,2S)-3-Azido-2-chloro-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-1-trityl-1H-imidazole 

Relevant academic research and scientific papers

New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues

New C2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(β-D-ribofuranosyl)imidazolium 7 and 1-(β-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared. For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)2 was employed. These new base modified nucleosides were devoid of activity, against HIV and cytotoxicity.