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【结 构 式】

【分子编号】18090

【品名】benzyl (1S)-1-[(4R,5R)-5-((1S)-1-[[(benzyloxy)carbonyl]amino]-2-phenylethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethylcarbamate

【CA登记号】

【 分 子 式 】C37H40N2O6

【 分 子 量 】608.73448

【元素组成】C 73.01% H 6.62% N 4.6% O 15.77%

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:(III)

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
Extended Information