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【结 构 式】

【分子编号】25250

【品名】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

【CA登记号】

【 分 子 式 】C14H23NO5Si

【 分 子 量 】313.42586

【元素组成】C 53.65% H 7.4% N 4.47% O 25.52% Si 8.96%

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:(III)

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
Extended Information