119139-11-6

Basic information

• Product Name: N'-benzyloxy-5--1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine
• CAS NO: 119139-11-6
• Molecular Weight: 507.544
• Mol File: 119139-11-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N'-benzyloxy-5--1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine(CAS DataBase Reference)
• NIST Chemistry Reference: N'-benzyloxy-5--1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine(119139-11-6)
• EPA Substance Registry System: N'-benzyloxy-5--1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine(119139-11-6)

Safety Data

• Hazardous Substances Data: 119139-11-6(Hazardous Substances Data)

Upstream product

• 50507-48-7 N'-benzyloxy-5-formamido-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine 
• 51806-20-3 1,1-diethoxy-2-iodoethane 

Downstream Products

• 115173-45-0 3-β-D-ribofuranosylazepinomycin 
• 119139-12-7 N'-benzyloxy-5-(2,2-diethoxyethylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine 

Relevant articles and documents

Purines. LXIII. Syntheses of azepinomycin, an antitumor antibiotic from Streptomyces species, and its 3-β-D-ribofuranoside and their 8-imino analogues

Three variants of a synthetic route to the antitumor antibiotic azepinomycin (3) from 1-substituted N'-alkoxy-5-formamidoimidazole-4- carboxamidine (type 10) are described. The synthesis started with the monocycles 10a-c and proceeded through the intermediates 11a-c, 12a-c, 13a- c, 14a-c, and 4a, b and 3-β-D-ribofuranosylazepinomycin (4c). The benzyl version (series a), including the permutation 14a → 15 → 3, was found to produce the antibiotic (3) most efficiently. The starting materials 10a-c were readily prepared from the 9-substituted adenines 7a-c via the N-oxides 8a-c and the 1-alkoxy derivatives 9a-c. The 8-imino analogues (17 and 18) of 3 and 4c were also synthesized from 12a and 12c, respectively.