新产品编号:1150623

Chemical Name: 1beta-(2,6,7-Trichloro-1H-naphtho[2,3-d]imidazol-1-yl)-D-ribofuranose
项目整合开发状态: Biological Testing
项目研究机构: University of Michigan (Originator)
合成路线:The hydrolysis of 6,7-dichloro-3-nitro-2-naphthoic acid ethyl ester (I) with NaOH in ethanol gives the expected free acid (II),which is treated with diphenylphosphoroazidate and triethylamine in DMF to yield 6,7-dichloro-3-nitro-2-naphthylamine (III).The reduction of (III) with H2 over RaNi in ehanol/ethyl acetate affords the corresponding diamine (IV),which is cyclized with thiocarbonyldi-imidazole (V) in refluxing benzene to give 6,7-dichloro-2,3-dihydro-1H-naphtho[2,3-d]imidazole-2-thione (VI).The methylation of (VI) with methyl iodide in dry DMF yields the corresponding methylsulfanyl derivative (VII),which is condensed with 1-O-acetyl-2,3,5-tri-O-ben-zoyl-beta-D-ribofuranose (VIII) by means of trimethylsilyl trifluoro-methanesulfonate (TMSOTf) and N,O-bis(trimethylsilyl)acetamide (BSA) in dichloromethane affording the benzoylated ribofuranoside (IX).The debenzoylation of (IX) with ammonia in methanol gives the free ribofuranoside (X),which is finally treated with Cl2/CCl4 in methanol to eliminate the methylsulfanyl group.