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【结 构 式】 
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【分子编号】23837 【品名】allyl (4S,5R,6S)-6-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-3-[[6-(2-hydroxyethyl)-1,1-dioxo-2H-naphtho[1,8-cd]isothiazol-2(1H)-yl]methyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C30H32N2O9S 【 分 子 量 】596.65816 【元素组成】C 60.39% H 5.41% N 4.7% O 24.13% S 5.37% |
合成路线1
该中间体在本合成路线中的序号：(XLIV)Mitsunobu coupling of hydroxymethyl carbapenem (XXX) with protected sultam (VIIIa) produced adduct (XLIII), which was desilylated with trifluoromethanesulfonic acid to give alcohol (XLIV). Conversion of (XLIV) to the corresponding triflate, followed by condensation with 1-carbamoylmethyl-4-aza-1-azoniabicyclo[2.2.2]octane trifluoromethanesulfonate (XLV) furnished bisam-monium salt (XLVI). Finally, cleavage of the allyl groups of (XLVI) in the presence of Pd catalyst yielded the title compound.
| 【1】 Morgan, J.D.; Wilkenning, R.R.; Santorelli, G.M.; Parker, D.L. Jr.; Hammond, M.L.; Wildonger, K.J.; Ratcliffe, R.W.; Blizzard, T.A.; Waddell, S.T.; Synthesis and properties of 2-(naphthosultamyl)met. Bioorg Med Chem Lett 1999, 9, 5, 679. |
| 【2】 Wilkening, R.R.; Ratcliffe, R.W.; Blizzard, T.A. (Merck & Co., Inc.); Carbapenem antibacterial cpds., compsns. containing such cpds. and methods of treatment. EP 0906313; JP 1999508279; US 5756725; WO 9740048 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIIIa) | 23835 | 6-[3-(trimethylsilyl)propyl]-2H-naphtho[1,8-cd]isothiazole-1,1(2H)-dione; 6-[2-[(trimethylsilyl)oxy]ethyl]-2H-naphtho[1,8-cd]isothiazole-1,1(2H)-dione | C15H19NO3SSi | 详情 | 详情 | |
| (XXX) | 23834 | allyl (4S,5R,6S)-6-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-3-(hydroxymethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C18H23NO7 | 详情 | 详情 | |
| (XLIII) | 30155 | allyl (4S,5R,6S)-6-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-3-[[1,1-dioxo-6-[3-(trimethylsilyl)propyl]-2H-naphtho[1,8-cd]isothiazol-2(1H)-yl]methyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C34H42N2O8SSi | 详情 | 详情 | |
| (XLIV) | 23837 | allyl (4S,5R,6S)-6-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-3-[[6-(2-hydroxyethyl)-1,1-dioxo-2H-naphtho[1,8-cd]isothiazol-2(1H)-yl]methyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C30H32N2O9S | 详情 | 详情 | |
| (XLV) | 30156 | 1-(2-amino-2-oxoethyl)-4-aza-1-azoniabicyclo[2.2.2]octane trifluoromethanesulfonate | C9H16F3N3O4S | 详情 | 详情 | |
| (XLVI) | 30157 | 1-[2-(2-[[(4S,5R,6S)-2-[(allyloxy)carbonyl]-6-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]methyl]-1,1-dioxo-1,2-dihydro-2H-naphtho[1,8-cd]isothiazol-6-yl)ethyl]-4-(2-amino-2-oxoethyl)-1,4-diazonia | C40H47F6N5O15S3 | 详情 | 详情 |