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【结 构 式】 
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【分子编号】39846 【品名】(6R,7S)-3-[[(aminocarbonyl)oxy]methyl]-7-[(5-amino-5-carboxypentanoyl)amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 【CA登记号】 |
【 分 子 式 】C16H22N4O9S 【 分 子 量 】446.43824 【元素组成】C 43.05% H 4.97% N 12.55% O 32.25% S 7.18% |
合成路线1
该中间体在本合成路线中的序号：(XXXIII)Fermentation of Streptomyces lactamdurans NRRL-3802 produces sodium 7beta-(D-5-amino-S-carboxyvaleramido)-3-carbamoyloxymethyl-7-methoxy-3-cephem-4-carboxylate (XXXIII), which is tosylated as usual to the N-tosyl derivative (XXXIV). The esterification of (XXXIV) with methyl chloromethyl ether (H) in CH2Cl2 yields the methoxymethyl ester (XXXV), which is finally treated first with 2-thienylcarbonyl chloride (E) on a 4-angstrom molecular sieve in dichloroethane, and then with HCl methanol.
| 【1】 Weinstock, L.M.; Preparation of 7-acylaminocephalosporin derivatives. DE 2456528; FR 2253022; GB 1480757; JP 50105687 . |
| 【2】 Castaner, J.; Loren, J.G.; Cefoxitin. Drugs Fut 1978, 3, 6, 434. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (E) | 15673 | 2-(2-thienyl)acetyl chloride; 2-Thiopheneacetyl chloride | 39098-97-0 | C6H5ClOS | 详情 | 详情 |
| (H) | 18319 | Chloro(methoxy)methane; Chloromethyl methyl ether | 107-30-2 | C2H5ClO | 详情 | 详情 |
| (XXXIII) | 39846 | (6R,7S)-3-[[(aminocarbonyl)oxy]methyl]-7-[(5-amino-5-carboxypentanoyl)amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C16H22N4O9S | 详情 | 详情 | |
| (XXXIV) | 39847 | (6R,7S)-3-[[(aminocarbonyl)oxy]methyl]-7-[(5-carboxy-5-[[(4-methylphenyl)sulfonyl]amino]pentanoyl)amino]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C23H28N4O11S2 | 详情 | 详情 | |
| (XXXV) | 39848 | methoxymethyl (6R,7S)-3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-7-[(6-(methoxymethoxy)-5-[[(4-methylphenyl)sulfonyl]amino]-6-oxohexanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C27H36N4O13S2 | 详情 | 详情 |