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【结 构 式】 
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【分子编号】25251 【品名】3-[(3aR,4R,6R,6aS)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]isoxazole; (3aS,4R,6R,6aR)-6-(3-isoxazolyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl methyl ether 【CA登记号】 |
【 分 子 式 】C11H15NO5 【 分 子 量 】241.24384 【元素组成】C 54.77% H 6.27% N 5.81% O 33.16% |
合成路线1
该中间体在本合成路线中的序号：(IV)The cyclization of ribofuranoside (I) with trimethylsilyl acetylene (II) by means of NBS in DMF gives the trimethylsilylisoxazole (III), which is desilylated with NaOH in methanol yielding the isoxazole (IV). Elimination of the isopropylidene protecting group of (IV) by passing through a Dowex 50 H+ column affords the dihydroxy compound (V), which is benzoylated with benzoyl chloridde and DMAP in pyridine giving the dibenzoyl derivative (VI). The condensation of (VI) with 2,6-dichloro-9H-purine (VII) in refluxing hexamethyldisilazane (HMDA) provides the purine derivative (VIII), which is treated with 0-methylhydroxylamine and triethylamine in refluxing dioxane yielding the adenosine derivative (IX). Finally, this compound is debenzoylated with ammonia in methanol.
| 【1】 Knutsen, L.; Olsen, U.B.; Roberts, S.M.; Varley, D.R.; Bowler, A.N. (Novo Nordisk A/S); Novel N-alkoxyadenine derivs. acting as cytokine inhibitors. WO 9801459 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 | |
| 15455 | (aminooxy)methane; O-methylhydroxylamine | 67-62-9 | CH5NO | 详情 | 详情 | |
| (I) | 25249 | (3aR,4R,6R,6aS)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde O-methyloxime | C10H17NO5 | 详情 | 详情 | |
| (II) | 23897 | ethynyl(trimethyl)silane；trimethylsilyl acetylene | 1066-54-2 | C5H10Si | 详情 | 详情 |
| (III) | 25250 | 3-[(3aR,4R,6R,6aS)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(trimethylsilyl)isoxazole; (3aS,4R,6R,6aR)-2,2-dimethyl-6-[5-(trimethylsilyl)-3-isoxazolyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl methyl ether | C14H23NO5Si | 详情 | 详情 | |
| (IV) | 25251 | 3-[(3aR,4R,6R,6aS)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]isoxazole; (3aS,4R,6R,6aR)-6-(3-isoxazolyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl methyl ether | C11H15NO5 | 详情 | 详情 | |
| (V) | 25252 | (2R,3S,4S,5R)-2-(3-isoxazolyl)-5-methoxytetrahydro-3,4-furandiol | C8H11NO5 | 详情 | 详情 | |
| (VI) | 25253 | (2R,3R,4R,5R)-4-(benzoyloxy)-2-(3-isoxazolyl)-5-methoxytetrahydro-3-furanyl benzoate | C22H19NO7 | 详情 | 详情 | |
| (VII) | 25254 | 2,6-dichloro-9H-purine | 5451-40-1 | C5H2Cl2N4 | 详情 | 详情 |
| (VIII) | 25255 | (2R,3R,4S,5R)-4-(benzoyloxy)-2-(2,6-dichloro-9H-purin-9-yl)-5-(3-isoxazolyl)tetrahydro-3-furanyl benzoate | C26H17Cl2N5O6 | 详情 | 详情 | |
| (IX) | 25256 | (2R,3R,4S,5R)-4-(benzoyloxy)-2-[2-chloro-6-(methoxyamino)-9H-purin-9-yl]-5-(3-isoxazolyl)tetrahydro-3-furanyl benzoate | C27H21ClN6O7 | 详情 | 详情 |