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【结 构 式】 
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【分子编号】18093 【品名】benzyl (1S)-1-([[(1S)-1-((4R,5R)-5-[(1S)-1-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-2-phenylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-2-phenylethyl]amino]carbonyl)-2-methylpropylcarbamate 【CA登记号】 |
【 分 子 式 】C47H58N4O8 【 分 子 量 】806.99968 【元素组成】C 69.95% H 7.24% N 6.94% O 15.86% |
合成路线1
该中间体在本合成路线中的序号：(VI)Diol (I) was protected as the isopropylidene ketal (III) by reaction with 2,2-dimethoxypropane (II) and p-toluenesulfonic acid. Then, the N-carbobenzoxy groups of (III) were eliminated by hydrogenolysis on Pd/C to give the diamine (IV), and this was coupled with N-carbobenzoxy-valine (V) using O-benzotriazol-1-yl-tetramethyluronium hexafluorophosphate (HBTU) to afford (VI). A new sequence of hydrogenolytic Cbz deprotection to give diamine (VII) and coupling with N-carbobenzoxy-alanine (VIII) and HBTU provided (IX). Finally, the target compound was obtained by hydrolysis of the isopropylidene ketal in methanol containing p-toluenesulfonic acid.
| 【1】 Lee, T.; et al.; Analysis of the S3 and S3' subsite specificities of feline immunodeficiency virus (FIV) protease: Development of a broad-based protease inhibitor efficacious against FIV, SIV, and HIV in vitro and ex vivo. Proc Natl Acad Sci USA 1998, 95, 3, 939-944. |
| 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) | 16587 | benzyl (1S,2R,3R,4S)-1-benzyl-4-[[(benzyloxy)carbonyl]amino]-2,3-dihydroxy-5-phenylpentylcarbamate | C34H36N2O6 | 详情 | 详情 | |
| (II) | 10722 | 1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane | 77-76-9 | C5H12O2 | 详情 | 详情 |
| (III) | 18090 | benzyl (1S)-1-[(4R,5R)-5-((1S)-1-[[(benzyloxy)carbonyl]amino]-2-phenylethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethylcarbamate | C37H40N2O6 | 详情 | 详情 | |
| (IV) | 18091 | (1S)-1-[(4R,5R)-5-[(1S)-1-amino-2-phenylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethylamine; (1S)-1-[(4R,5R)-5-[(1S)-1-amino-2-phenylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenyl-1-ethanamine | C21H28N2O2 | 详情 | 详情 | |
| (V) | 18092 | (2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutyric acid | C13H17NO4 | 详情 | 详情 | |
| (VI) | 18093 | benzyl (1S)-1-([[(1S)-1-((4R,5R)-5-[(1S)-1-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-2-phenylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-2-phenylethyl]amino]carbonyl)-2-methylpropylcarbamate | C47H58N4O8 | 详情 | 详情 | |
| (VII) | 18094 | (2S)-2-amino-N-[(1S)-1-[(4R,5R)-5-((1S)-1-[[(2S)-2-amino-3-methylbutanoyl]amino]-2-phenylethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethyl]-3-methylbutanamide | C31H46N4O4 | 详情 | 详情 | |
| (VIII) | 10445 | N-Carbobenzyloxy-L-alanine;N-Benzyloxycarbonyl-L-alanine;Carbobenzyloxy-L-alanine;Z-L-Alanine;Z-Ala-OH;BenzyloxycarbonylLalanine;N-Cbz-L-alanine | 1142-20-7 | C11H13NO4 | 详情 | 详情 |
| (IX) | 18095 | benzyl (1S)-2-[((1S)-1-[[((1S)-1-[(4R,5R)-5-[(1S,4S,7S)-1-benzyl-4-isopropyl-7-methyl-3,6,9-trioxo-11-phenyl-10-oxa-2,5,8-triazaundec-1-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethyl)amino]carbonyl]-2-methylpropyl)amino]-1-methyl-2-oxoethylcarbam | C53H68N6O10 | 详情 | 详情 |