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【结 构 式】

【分子编号】25260

【品名】(2R,3R,4R,5S)-5-(acetoxy)-4-(benzoyloxy)-2-vinyltetrahydro-3-furanyl benzoate

【CA登记号】

【 分 子 式 】C22H20O7

【 分 子 量 】396.3966

【元素组成】C 66.66% H 5.09% O 28.25%

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:(VI)

The oxidation of 1-O-mehyl 2,3-isopropylidene-D-ribofuranoside (I) gives the corresponding aldehyde (II), which is condensed with methyltriphenylphosphonium bromide by means of butyllithium in THF yielding methyl 5-deoxy-2,3-isopropylidene-5-methylene-D-ribofuranoside (III). Elimination of the isopropylidene protecting group by passing through an Amberlyst resin (acid form) affords the free ribofuranoside (IV), which is benzoylated with benzoyl chloride and triethylamine in dichloromethane to afford the dibenzoyl derivative (V). The methyl ribofuranoside (V) was converted into the 1-O-acetyl derivative (VI) and condensed with 2,6-dichloro-9H-purine (VII) by heating at 150 C to provide the dichloropurine derivative (VIII), which is treated with O-methylhydroxylamine and triethylamine to afford 2',3'-di-O-benzoyl-2-chloro-5'-deoxy-N-methoxy-5'-methyleneadenosine (IX). Finally, this compound is debenzoylated with ammonia in methanol.

1 Lau, J.; Knutsen, L.J.S. (Novo Nordisk A/S); Chemical cpds., their preparation and use. EP 0719275; JP 1999511436; US 5589467; WO 9507921 .
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) 10017 [(3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol 4099-85-8 C9H16O5 详情 详情
(II) 10018 (3aR,4S,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde C9H14O5 详情 详情
(III) 25257 (3aS,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyltetrahydrofuro[3,4-d][1,3]dioxole; (3aS,4R,6R,6aR)-2,2-dimethyl-6-vinyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl methyl ether C10H16O4 详情 详情
(IV) 25258 (2R,3S,4S,5R)-2-methoxy-5-vinyltetrahydro-3,4-furandiol C7H12O4 详情 详情
(V) 25259 (2R,3R,4R,5R)-4-(benzoyloxy)-2-methoxy-5-vinyltetrahydro-3-furanyl benzoate C21H20O6 详情 详情
(VI) 25260 (2R,3R,4R,5S)-5-(acetoxy)-4-(benzoyloxy)-2-vinyltetrahydro-3-furanyl benzoate C22H20O7 详情 详情
(VII) 25254 2,6-dichloro-9H-purine 5451-40-1 C5H2Cl2N4 详情 详情
(VIII) 25261 (2R,3R,4S,5R)-4-(benzoyloxy)-2-(2,6-dichloro-9H-purin-9-yl)-5-vinyltetrahydro-3-furanyl benzoate C25H18Cl2N4O5 详情 详情
(IX) 25262 (2R,3R,4S,5R)-4-(benzoyloxy)-2-[2-chloro-6-(methoxyamino)-9H-purin-9-yl]-5-vinyltetrahydro-3-furanyl benzoate C26H22ClN5O6 详情 详情
Extended Information