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【结 构 式】

【分子编号】15843

【品名】(1S,2S)-2-[[(benzyloxy)carbonyl]amino]-1-([(4R)-4-[(tert-butylamino)carbonyl]-1,3-thiazolidin-3-yl]carbonyl)-3-phenylpropyl (2R)-2-[[2-(5-isoquinolinyloxy)acetyl]amino]-3-(methylsulfanyl)propanoate

【CA登记号】

【 分 子 式 】C41H47N5O8S2

【 分 子 量 】801.98508

【元素组成】C 61.4% H 5.91% N 8.73% O 15.96% S 8%

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:(XI)

2) The intermediate (V) of the preceding synthesis is submitted to a deprotection - protection sequence [hydrolysis with HCl in dioxane and protection with benzyl succinimidyl carbonate (PhCH2-OSu)] giving the benzyloxycarbonyl protected compound (IX), which is condensed with (VI) by means of DCC and dimethylaminopyridine (DMAP) to yield (X) [the ester isomer of (VII)]. The deprotection of (X) with HCl and condensation with (VIII) by means of HBOT and DCC as before affords (XI) [the benzyloxycarbonyl protected prodrug of KNI-272], which is deprotected with trifluoroacetic acid (TFA)/anisole and HCl affording the ester prodrug (XII). Finally, this compound is converted into KNI-272 by incubation at 37 C in a phosphate buffered saline at pH 7.4.

1 Kimura, T.; Ohtake, J.; Nakata, S.; Enomoto, H.; Moriwaki, H.; Akaji, K.; Kiso, Y.; Synthesis and prodrugs of HIV protease inhibitors. Peptide Chem 1994, 157-60.
2 Ireland, C.D.; Castaner, J.; KNI-272. Drugs Fut 1996, 21, 10, 1022.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 15837 tert-Butyl N-((1S,2S)-1-benzyl-3-[(4R)-4-[(tert-butylamino)carbonyl]-1,3-thiazolan-3-yl]-2-hydroxy-3-oxopropyl)carbamate C23H35N3O5S 详情 详情
(VI) 15838 (2R)-2-[(tert-butoxycarbonyl)amino]-3-(methylsulfanyl)propionic acid C9H17NO4S 详情 详情
(VIII) 15840 2-(5-isoquinolinyloxy)acetic acid C11H9NO3 详情 详情
(IX) 15841 benzyl N-((1S,2S)-1-benzyl-3-[(4R)-4-[(tert-butylamino)carbonyl]-1,3-thiazolan-3-yl]-2-hydroxy-3-oxopropyl)carbamate C26H33N3O5S 详情 详情
(X) 15842 (1S,2S)-2-[[(benzyloxy)carbonyl]amino]-1-([(4R)-4-[(tert-butylamino)carbonyl]-1,3-thiazolidin-3-yl]carbonyl)-3-phenylpropyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(methylsulfanyl)propanoate C35H48N4O8S2 详情 详情
(XI) 15843 (1S,2S)-2-[[(benzyloxy)carbonyl]amino]-1-([(4R)-4-[(tert-butylamino)carbonyl]-1,3-thiazolidin-3-yl]carbonyl)-3-phenylpropyl (2R)-2-[[2-(5-isoquinolinyloxy)acetyl]amino]-3-(methylsulfanyl)propanoate C41H47N5O8S2 详情 详情
(XII) 15844 (1S,2S)-2-amino-1-([(4R)-4-[(tert-butylamino)carbonyl]-1,3-thiazolidin-3-yl]carbonyl)-3-phenylpropyl (2R)-2-[[2-(5-isoquinolinyloxy)acetyl]amino]-3-(methylsulfanyl)propanoate C33H41N5O6S2 详情 详情
Extended Information