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【结 构 式】 
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【分子编号】14542 【品名】tert-butyl (1S,2S)-1-benzyl-2-hydroxy-2-(1,3-thiazol-2-yl)ethylcarbamate 【CA登记号】 |
【 分 子 式 】C17H22N2O3S 【 分 子 量 】334.43936 【元素组成】C 61.05% H 6.63% N 8.38% O 14.35% S 9.59% |
合成路线1
该中间体在本合成路线中的序号：(XXVII)3) The condensation of N-(tert-butoxycarbonyl)-L-phenylalaninal (XXV) with 2-(trimethylsilyl)thiazole (XXVI) by means of tetrabutylammonium fluoride gives the thiazole derivative (XXVII), which is cleaved by reaction with methyl iodide (formation of the thiazolium derivative) and treated with NaBH4 and HgCl2 to afford the protected 3(S)-amino-2(S)-hydroxy-4-phenylbutanal (XXVIII). Finally, this compound is reductocondensed with isoquinoline (XI) by means of sodium cyanoborohydride to yield the protected condensation product (XII), already obtained in scheme 16810301a.
| 【1】 Parkes, K.E.B.; Bushnell, D.J.; Crackett, P.H.; et al.; Studies toward the large-scale synthesis of the HIV proteinase inhibitor Ro 31-8959. J Org Chem 1994, 59, 13, 3656. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 14527 | (3S,4aS,8aS)-N-(tert-butyl)-2-((2R,3S)-3-[[(2,2-dimethylpropanoyl)oxy]amino]-2-hydroxy-4-phenylbutyl)decahydro-3-isoquinolinecarboxamide | C29H47N3O4 | 详情 | 详情 | |
| (XXV) | 14540 | tert-butyl N-[(1S)-1-benzyl-2-oxoethyl]carbamate | C14H19NO3 | 详情 | 详情 | |
| (XXVI) | 10720 | 2-(Trimethylsilyl)-1,3-thiazole | 79265-30-8 | C6H11NSSi | 详情 | 详情 |
| (XXVII) | 14542 | tert-butyl (1S,2S)-1-benzyl-2-hydroxy-2-(1,3-thiazol-2-yl)ethylcarbamate | C17H22N2O3S | 详情 | 详情 | |
| (XXVIII) | 14543 | tert-butyl N-[(1S,2S)-1-benzyl-2-hydroxy-3-oxopropyl]carbamate | C15H21NO4 | 详情 | 详情 |