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【结 构 式】

【分子编号】54604

【品名】benzyl (1S)-2-phenyl-1-(1,3-thiazolidin-2-yl)ethylcarbamate

【CA登记号】

【 分 子 式 】C19H22N2O2S

【 分 子 量 】342.46196

【元素组成】C 66.64% H 6.48% N 8.18% O 9.34% S 9.36%

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:(XX)

The reduction of N-(benzyloxycarbonyl)-L-phenylalanine (XVI) gives the corresponding aldehyde (XVII), which is cyclized with 2-sulfanylethylamine (XVIII) to yield the thiazolidine (XIX). The dehydrogenation of (XIX) by means of MnO2 affords the thiazole derivative (XX). Finally, the amino group of (XX) is deprotected with HBr to afford the desired intermediate, 2-phenyl-1(S)-(2-thiazolyl)ethylamine (XXI). Alternatively, N-(benzyloxycarbonyl)-L-phenylalanine (XVI) can be converted into the corresponding amide (XXII), which is treated with the Lawesson's reagent to yield the thioamide (XXIII). Finally, the cyclization of (XXIII) with 2-bromoacetaldehyde (XXIV) gives already reported thiazole derivative (XX) (partial racemization occurs during the synthetic process). Enantiomeric separation takes place in a later stage.

1 Roux, F.; et al.; Synthesis of dolastatin-10 and [R-Doe]-dolastatin-10. Tetrahedron 1994, 50, 18, 5345.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
54607 (1S)-2-phenyl-1-(1,3-thiazol-2-yl)-1-ethanamine; (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylamine C11H12N2S 详情 详情
(XVI) 14505 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropionic acid; N-Carbobenzyloxy-L-phenylalanine; N-Cbz-L-Phenylalanine 1161-13-3 C17H17NO4 详情 详情
(XVII) 16586 benzyl N-[(1S)-1-benzyl-2-oxoethyl]carbamate C17H17NO3 详情 详情
(XVIII) 13186 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine 60-23-1 C2H7NS 详情 详情
(XX) 54604 benzyl (1S)-2-phenyl-1-(1,3-thiazolidin-2-yl)ethylcarbamate C19H22N2O2S 详情 详情
(XXI) 24802 2-bromoacetaldehyde C2H3BrO 详情 详情
(XXII) 54603 benzyl (1S)-2-amino-1-benzyl-2-oxoethylcarbamate 4801-80-3 C17H18N2O3 详情 详情
(XXIII) 54605 benzyl (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylcarbamate C19H18N2O2S 详情 详情
(XXIV) 54606 benzyl (1S)-2-amino-1-benzyl-2-thioxoethylcarbamate C17H18N2O2S 详情 详情
Extended Information