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【结 构 式】 
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【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% |
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 |