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【结 构 式】

【分子编号】28469

【品名】(2S,3R)-3-(1,3-benzodioxol-5-yl)-5,5-diethoxy-2-pentanol

【CA登记号】

【 分 子 式 】C16H24O5

【 分 子 量 】296.36356

【元素组成】C 64.84% H 8.16% O 26.99%

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:(IV)

Intermediate amine (X) was prepared as follows: Alkylation of 3,4-(methylenedioxy)phenylacetone (I) with iodoacetaldehyde diethyl acetal (II) provided racemic ketone (III), which was diastereoselectively reduced to alcohol (IV) with L-Selectride. Resolution was effected by esterification with (R)-alpha-methoxyphenylacetic acid, followed by chromatographic separation of the diastereoisomeric esters. The required isomer (V) was hydrolyzed under alkaline conditions and the resulting alcohol was converted to mesylate (VI) by treatment with methanesulfonyl chloride and Et3N. Displacement of the mesylate group of (VI) with NaN3 with inversion of the configuration yielded azide (VII), which was reduced to amine (VIII) using PPh3. Then, reductive condensation of (VIII) with 2-naphthalenecarboxaldehyde in the presence of NaBH4 afforded the secondary amine (X).

1 Aoyama, T.; et al.; A new class of highly potent farnesyl diphosphate-competitive inhibitors of farnesyltransferase. J Med Chem 1998, 41, 2, 143.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 28466 1-(1,3-benzodioxol-5-yl)acetone 4676-39-5 C10H10O3 详情 详情
(II) 28467 1,1-diethoxy-2-iodoethane C6H13IO2 详情 详情
(III) 28468 3-(1,3-benzodioxol-5-yl)-5,5-diethoxy-2-pentanone C16H22O5 详情 详情
(IV) 28469 (2S,3R)-3-(1,3-benzodioxol-5-yl)-5,5-diethoxy-2-pentanol C16H24O5 详情 详情
(V) 28470 (1S,2R)-2-(1,3-benzodioxol-5-yl)-4,4-diethoxy-1-methylbutyl (2R)-2-methoxy-2-phenylethanoate C25H32O7 详情 详情
(VI) 28471 (1S,2R)-2-(1,3-benzodioxol-5-yl)-4,4-diethoxy-1-methylbutyl methanesulfonate C17H26O7S 详情 详情
(VII) 28472 5-[(1R)-1-[(1R)-1-azidoethyl]-3,3-diethoxypropyl]-1,3-benzodioxole C16H23N3O4 详情 详情
(VIII) 28473 (1R,2R)-2-(1,3-benzodioxol-5-yl)-4,4-diethoxy-1-methylbutylamine C16H25NO4 详情 详情
(IX) 28474 2-Naphthaldehyde 66-99-9 C11H8O 详情 详情
(X) 28475 (2R,3R)-3-(1,3-benzodioxol-5-yl)-5,5-diethoxy-N-(2-naphthylmethyl)-2-pentanamine C27H33NO4 详情 详情
Extended Information