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【结 构 式】

【分子编号】32610

【品名】allyl (2R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-(2-hydroxyethyl)-1-pyrrolidinecarboxylate

【CA登记号】

【 分 子 式 】C16H31NO4Si

【 分 子 量 】329.51198

【元素组成】C 58.32% H 9.48% N 4.25% O 19.42% Si 8.52%

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:(VII)

Swern oxidation of protected (hydroxymethyl)pyrrolidine (I), followed by Wittig condensation of the resulting aldehyde (II) with methylene triphenylphosphorane provided vinylpyrrolidine (III). Hydroboration of (III) with 9-borabicyclo[3.3.1]nonane and subsequent oxidative treatment with sodium perborate gave alcohol (IV). Interconversion of the N-benzyl protecting group for an allyloxycarbonyl group was achieved by catalytic hydrogenation and then treatment of the deprotected amine (V) with allyloxycarbonyl chloride (VI). Alcohol (VII) was activated as the corresponding mesylate (VIII), which was condensed with imidazole (IX) in the presence of t-BuOK to afford the N-alkylated imidazole (X). Acid deprotection of the silyl ether of (X) yielded the corresponding secondary alcohol, which was further converted to mesylate (XI). Subsequent displacement in (XI) by potassium thioacetate furnished the thioacetate ester (XII).

1 Barrett, D.; Azami, H.; Matsuda, K.; et al.; Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems. Part III: Novel 2-alkyl substituents containing cationic heteroaromatics linked via a C-N bond. Bioorg Med Chem 1999, 7, 8, 1665.
2 Murata, M.; Tsutsumi, H.; Matsuda, K.; Hattori, K.; Nakajima, T. (Fujisawa Pharmaceutical Co., Ltd.); Substd. 3-pyrrolidinylthio-carbapenems as antimicrobial agents. EP 0636133; JP 1995505650; WO 9321186 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12893 Ethanethioic S-acid C2H4OS 详情 详情
38115 3-[(chlorocarbonyl)oxy]-1-propene 2937-50-0 C4H5ClO2 详情 详情
(I) 32605 ((2S,4S)-1-benzyl-4-[[tert-butyl(dimethyl)silyl]oxy]pyrrolidinyl)methanol C18H31NO2Si 详情 详情
(II) 32606 (2S,4S)-1-benzyl-4-[[tert-butyl(dimethyl)silyl]oxy]-2-pyrrolidinecarbaldehyde C18H29NO2Si 详情 详情
(III) 32607 (2S,4S)-1-benzyl-4-[[tert-butyl(dimethyl)silyl]oxy]-2-vinylpyrrolidine; (3S,5S)-1-benzyl-5-vinylpyrrolidinyl tert-butyl(dimethyl)silyl ether C19H31NOSi 详情 详情
(IV) 32608 2-((2R,4S)-1-benzyl-4-[[tert-butyl(dimethyl)silyl]oxy]pyrrolidinyl)-1-ethanol C19H33NO2Si 详情 详情
(V) 32609 2-((2R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]pyrrolidinyl)-1-ethanol C12H27NO2Si 详情 详情
(VII) 32610 allyl (2R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-(2-hydroxyethyl)-1-pyrrolidinecarboxylate C16H31NO4Si 详情 详情
(VIII) 32611 allyl (2R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-[2-[(methylsulfonyl)oxy]ethyl]-1-pyrrolidinecarboxylate C17H33NO6SSi 详情 详情
(IX) 10255 Imidazole; 1H-Imidazole 288-32-4 C3H4N2 详情 详情
(X) 32612 allyl (2R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-[2-(1H-imidazol-1-yl)ethyl]-1-pyrrolidinecarboxylate C19H33N3O3Si 详情 详情
(XI) 32613 allyl (2R,4S)-2-[2-(1H-imidazol-1-yl)ethyl]-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylate C14H21N3O5S 详情 详情
(XII) 31614 (3S)-5-chloro-3-([[(1S,2R,3S)-1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl]amino]carbonyl)-5-hexenoic acid C21H36ClNO5 详情 详情
Extended Information