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【结 构 式】 
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【分子编号】61479 【品名】benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-8-oxo-3-((E)-2-{[(trifluoromethyl)sulfonyl]oxy}ethenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C52H43ClF3N5O10S3 【 分 子 量 】1086.5870296 【元素组成】C 57.48% H 3.99% Cl 3.26% F 5.25% N 6.45% O 14.72% S 8.85% |
合成路线1
该中间体在本合成路线中的序号：(VI)Coupling of the amino cephem derivative (I) with oximino acid (II) by means of POCl3/pyridine produces amide (III). Subsequent condensation of (III) with bis(dimethylamino)t-butoxymethane affords enamine (IV), which is further hydrolyzed to aldehyde (V) under acidic conditions. Treatment of aldehyde (V) with trifluoromethanesulfonic anhydride and pyridine produces the vinyl triflate (VI)
| 【1】 Lee, C.; Kim, G.; Jang, Y.; Koo, K.; Cho, Y.; Youn, H.; Synthesis and antibacterial activities of LB11058, a novel anti-MRSA cephalosporin antibiotic. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-329. |
| 【2】 Lee, S.-H.; Lee, C.-S.; Ryu, E.-J.; Jang, Y.-J.; Kim, G.-T.; Cho, Y.-r.; Joo, H.-Y.; Shin, J.-E.; Koo, K.-D. (LG Chem Ltd.); Novel cephalosporin cpds. and process for preparing the same. WO 0372582 . |
| 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) | 61475 | benzhydryl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C21H20N2O3S | 详情 | 详情 | |
| (II) | 38203 | 2-[2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl]-2-[(trityloxy)imino]acetic acid | C29H26ClN3O5S | 详情 | 详情 | |
| (III) | 61476 | benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C50H44ClN5O7S2 | 详情 | 详情 | |
| (IV) | 61477 | benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-3-[(E)-2-(dimethylamino)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C53H49ClN6O7S2 | 详情 | 详情 | |
| (V) | 61478 | benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-8-oxo-3-(3-oxopropyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C52H46ClN5O8S2 | 详情 | 详情 | |
| (VI) | 61479 | benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-8-oxo-3-((E)-2-{[(trifluoromethyl)sulfonyl]oxy}ethenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C52H43ClF3N5O10S3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)Displacement of the triflate group of (VI) with the pyrimidinyl thiol (VII) yields the vinyl sulfide (VIII). Then, deprotection of (VIII) by means of trifluoroacetic acid and triethylsilane gives rise to the title compound
| 【1】 Lee, C.; Kim, G.; Jang, Y.; Koo, K.; Cho, Y.; Youn, H.; Synthesis and antibacterial activities of LB11058, a novel anti-MRSA cephalosporin antibiotic. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-329. |
| 【2】 Lee, S.-H.; Lee, C.-S.; Ryu, E.-J.; Jang, Y.-J.; Kim, G.-T.; Cho, Y.-r.; Joo, H.-Y.; Shin, J.-E.; Koo, K.-D. (LG Chem Ltd.); Novel cephalosporin cpds. and process for preparing the same. WO 0372582 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 61479 | benzhydryl (6R,7R)-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-8-oxo-3-((E)-2-{[(trifluoromethyl)sulfonyl]oxy}ethenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C52H43ClF3N5O10S3 | 详情 | 详情 | |
| (VII) | 61480 | 2-amino-6-sulfanyl-4-pyrimidinol | C4H5N3OS | 详情 | 详情 | |
| (VIII) | 61481 | benzhydryl (6R,7R)-3-{(E)-2-[(2-amino-6-hydroxy-4-pyrimidinyl)sulfanyl]ethenyl}-7-({2-{2-[(tert-butoxycarbonyl)amino]-5-chloro-1,3-thiazol-4-yl}-2-[(trityloxy)imino]acetyl}amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C55H47ClN8O8S3 | 详情 | 详情 |