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【结 构 式】

【分子编号】12802

【品名】[(2R,3S,5R)-3-hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydro-2-furanyl]methyl benzoate

【CA登记号】

【 分 子 式 】C17H16N4O5

【 分 子 量 】356.338

【元素组成】C 57.3% H 4.53% N 15.72% O 22.45%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

5) The benzoylation of 2'-deoxyinosine (I) with benzoyl chloride in pyridine gives the 5'-O-benzoyl derivative (II), which is treated with 1,1'-thiocarbonyldiimidazole (DTI) in DMF to afford the 2'-O-thiocarbonyl derivative (III). The reaction of (III) with bis(tributyltin)oxide, polymethylhydroxysilane and AIBN in refluxing dioxane yields 5'-O-benzoyl-2',3'-dideoxyinosine (IV), which is finally deprotected with anhydrous NH3 in methanol. Another microbial conversion of 2',3'-dideoxyuridine to 2',3'-dideoxyinosine by transdideoxyribosylation with hypoxanthine in a culture medium of Escherichia coli ATCC 10798 is described, and industrially applicable methods for the purification of enzymatically or microbially obtained dideoxyinosines are reported.

1 Tanabe, T.; Otani, M.; Arai, M.; Yukawa, T. (Ajinomoto Co., Inc.); Method for the purification of dideoxyinosine. JP 1989175991 .
2 Tanabe, T.; Otani, M.; Yukawa, T. (Ajinomoto Co., Inc.); Method for the purification of dideoxyinosine. JP 1989165390 .
3 Prous, J.; Castaner, J.; DIDEOXYINOSINE. Drugs Fut 1990, 15, 6, 569.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 12801 9-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-9H-purin-6-ol 890-38-0 C10H12N4O4 详情 详情
(II) 12802 [(2R,3S,5R)-3-hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydro-2-furanyl]methyl benzoate C17H16N4O5 详情 详情
(III) 12803 [(2R,3S,5R)-5-(6-hydroxy-9H-purin-9-yl)-3-[(1H-imidazol-1-ylcarbothioyl)oxy]tetrahydro-2-furanyl]methyl benzoate C21H18N6O5S 详情 详情
(IV) 12804 [(2S,5R)-5-(6-hydroxy-9H-purin-9-yl)tetrahydro-2-furanyl]methyl benzoate C17H16N4O4 详情 详情
Extended Information