【结 构 式】 |
【分子编号】54606 【品名】benzyl (1S)-2-amino-1-benzyl-2-thioxoethylcarbamate 【CA登记号】 |
【 分 子 式 】C17H18N2O2S 【 分 子 量 】314.4082 【元素组成】C 64.94% H 5.77% N 8.91% O 10.18% S 10.2% |
合成路线1
该中间体在本合成路线中的序号:(XXIV)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 |