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【结 构 式】 
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【分子编号】16077 【品名】4-methoxybenzyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(aminosulfonyl)amino]methyl]-1-(tert-butoxycarbonyl)pyrrolidinyl]sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C28H40N4O9S2 【 分 子 量 】640.77916 【元素组成】C 52.48% H 6.29% N 8.74% O 22.47% S 10.01% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of (1R,6S)-6-[1(R)-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylic acid 4-methoxybenzyl ester (I) with diphenyl chlorophosphate (II) and ethyl diisopropylamine in acetonitrile gives the corresponding penem diphenylphosphate (III), which is condensed with 1-(tert-butoxycarbonyl)-2(S)-sulfamoylaminomethyl)pyrrolidine-4(S)-thio l (IV) by means of ethyl diisopropylamine in the same solvent, yielding compound (V), which is finally treated with AlCl3 to eliminate the protecting groups to obtain S-4661.
| 【1】 Sendo, Y.; Kii, M.; Nishitani, Y.; Irie, T.; Nishino, Y. (Shionogi & Co., Ltd.); A production method for sulfamide. EP 0557122 . |
| 【2】 Castaner, J.; Mealy, N.; Rabasseda, X.; S-4661. Drugs Fut 1995, 20, 4, 367. |
| 【3】 Nishitani, Y.; Irie, T.; Nishino, Y. (Shionogi & Co. Ltd.); A pyrrolidylthiocarbapenem derivative. EP 0528678; JP 1993294970; US 5317016 . |
| 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) | 16073 | 4-methoxybenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate | C18H21NO6 | 详情 | 详情 | |
| (II) | 16074 | Diphenyl phosphoryl chloride; 1,1'-Diphenylphosphoryl chloride; Chlorodiphenyl Phosphate; Diphenyl chlorophosphate; Diphenylchlorophosphate | 2524-64-3 | C12H10ClO3P | 详情 | 详情 |
| (III) | 16075 | 4-methoxybenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C30H30NO9P | 详情 | 详情 | |
| (IV) | 16076 | tert-butyl (2S,4S)-2-[[(aminosulfonyl)amino]methyl]-4-sulfanyltetrahydro-1H-pyrrole-1-carboxylate | C10H21N3O4S2 | 详情 | 详情 | |
| (V) | 16077 | 4-methoxybenzyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(aminosulfonyl)amino]methyl]-1-(tert-butoxycarbonyl)pyrrolidinyl]sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C28H40N4O9S2 | 详情 | 详情 |