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【结 构 式】

【分子编号】33167

【品名】3,5-dibromo-1-cyclopentene

【CA登记号】

【 分 子 式 】C5H6Br2

【 分 子 量 】225.91064

【元素组成】C 26.58% H 2.68% Br 70.74%

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:(II)

The reaction of cyclopentadiene (I) with Br2 gives 1,4-dibromo-2-cyclopentene (II), which is treated with potassium acetate in tert-butanol yielding 1,4-diacetoxy-2-cyclopentene (III). The hydrolysis of (III) with KHCO3 in methanol affords 2-cyclopentene-1,4-diol (IV) as a mixture of the cis and trans isomers. The treatment of (cis/trans) (IV) or (cis) (IV) with pancreatin, vinyl acetate (V) and triethylamine gives (1R,4S)-4-acetoxy-2-cyclopenten-1-ol (VI), which is hydrogenated with H2 over RaNi in ethanol to yield the corresponding saturated (1S,3R)-3-acetoxycyclopentanol (VII). The reaction of (VII) with methanesulfonyl chloride and TEA in dichloromethane affords the corresponding mesylate (VIII), which is condensed with adenine (IX) by means of NaH in hot DMF providing the final intermediate (X). Finally, this compound is deacetylated with HCl in refluxing ethanol.

1 Borcherding, D.R.; et al.; Carbocyclic nucleosides as inhibitors of human Tumor Necrosis Factor-alpha production: Effects of the stereoisomers of (3-hydroxycyclopentyl)adenines. J Med Chem 1996, 39, 13, 2615.
2 Watson, T.J.N.; et al.; Development of the carbocyclic nucleoside MDL 201449A. A tumor necrosis factor-alpha inhibitor. Org Process Res Dev 1998, 2, 6, 357.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(cis/trans)(IV) 21533 4-cyclopentene-1,3-diol C5H8O2 详情 详情
(cis)(IV) 33168 (1R,3S)-4-cyclopentene-1,3-diol C5H8O2 详情 详情
(I) 11183 1,3-Cyclopentadiene C5H6 详情 详情
(II) 33167 3,5-dibromo-1-cyclopentene C5H6Br2 详情 详情
(III) 21534 4-(acetoxy)-2-cyclopenten-1-yl acetate C9H12O4 详情 详情
(V) 24543 vinyl acetate 108-05-4 C4H6O2 详情 详情
(VI) 33169 (1S,4R)-4-hydroxy-2-cyclopenten-1-yl acetate C7H10O3 详情 详情
(VII) 33170 (1R,3S)-3-hydroxycyclopentyl acetate C7H12O3 详情 详情
(VIII) 33171 (1R,3S)-3-[(methylsulfonyl)oxy]cyclopentyl acetate C8H14O5S 详情 详情
(IX) 10343 9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine 73-24-5 C5H5N5 详情 详情
(X) 33172 (1R,3R)-3-(6-amino-9H-purin-9-yl)cyclopentyl acetate C12H15N5O2 详情 详情
Extended Information