【结 构 式】 |
【分子编号】12804 【品名】[(2S,5R)-5-(6-hydroxy-9H-purin-9-yl)tetrahydro-2-furanyl]methyl benzoate 【CA登记号】 |
【 分 子 式 】C17H16N4O4 【 分 子 量 】340.3386 【元素组成】C 60% H 4.74% N 16.46% O 18.8% |
合成路线1
该中间体在本合成路线中的序号:(IV)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 |