161824-93-7

Basic information

• Product Name: 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine
• Synonyms: 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine
• CAS NO: 161824-93-7
• Molecular Weight: 464.518
• Mol File: 161824-93-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine(161824-93-7)
• EPA Substance Registry System: 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine(161824-93-7)

Safety Data

• Hazardous Substances Data: 161824-93-7(Hazardous Substances Data)

Upstream product

• 1463-10-1 5-Methyluridine 
• 161824-89-1 1-<2',3'-Dihydroxy-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N³-(4-methoxybenzyl)-5-methyluracil 
• 161824-97-1 1-<2'-O,3'-O-Cyclopentyl-5'-O-(4-methoxybenzyl)-β-D-erythro-pentofuranosyl>-N³-(4-methoxybenzyl)-5-methyluracil 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 161824-82-4 1-(2'-O,3'-O-Cyclopentyl-5'-hydroxy-β-D-erythro-pentofuranosyl)-5-methyluracil 

Downstream Products

• 3056-17-5 stavudin 

Relevant articles and documents

A Facile Route to Pyrimidine-Based Nucleoside Olefins: Application to the Synthesis of d4T (Stavudine)

An efficient synthetic route to nucleoside olefins in the uridine, cytidine, and thymidine series is described which utilizes the Garegg-Samuelsson iodine/triphenylphosphine/imidazole-promoted deoxygenation of the 2',3'-hydroxyl groups as the key step.Cyclopentadiene ketal protection was employed for all the nucleoside 2',3'-hydroxyls to facilitate blocking of the 5'-hydroxyl and the pyrimidine nitrogens with the benzyl or 4-methoxybenzyl (PMB) groups.Deblocking of the cyclopentylidene group followed by olefination of the resulting diols provided protected nucleoside olefins 18-20.Starting with 5-methyluridine 4 and utilizing the 4-methoxybenzyl group for 5',N3 protection, the overall scheme provided the anti-HIV compound d4T (1) after deprotection of the PMB groups.The dibenzylhypoxanthine nucleoside diol 17 derived from inosine gave either unreacted starting material or decomposition products under several sets of conditions.