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【结 构 式】 
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【分子编号】31607 【品名】1-(2-amino-2-oxoethyl)-4-[2-(1,1-dioxo-1,2-dihydro-2H-naphtho[1,8-cd]isothiazol-6-yl)ethyl]-1,4-diazoniabicyclo[2.2.2]octane di(trifluoromethanesulfonate) 【CA登记号】 |
【 分 子 式 】C22H26F6N4O9S3 【 分 子 量 】700.6584192 【元素组成】C 37.71% H 3.74% F 16.27% N 8% O 20.55% S 13.73% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The condensation of azetidinone (I) with carbonate (II) by means of TiCl4 and tributylamine in toluene gives the addition product (III), which is desilylated with HCl in aqueous acetonitrile and resilylated again with Tes-Cl and imidazole in toluene/acetonitrile yielding the silyl ether (IV). The condensation of (IV) with the oxalyl derivative (V) by means of pyridine in toluene affords the addition compound (VI), which is cyclized by means of P(OEt)3 in hot heptane giving the carbapenem compound (VII). The condensation of (VII) with naphthosultam (VIII) by means of palladium acetate and P(OBu)3 affords the protected target compound (IX), which is finally desilylated with aqueous Tf-OH, debenzylated with H2 over Pd/C, and treated with sodium benzenesulfonate to obtain the sulfonate salt of the target compound.
| 【1】 Humphrey, G.R.; et al.; Efficient and practical synthesis of a potent anti-MRSA beta-methylcarbapenem containing a releasable side chain. J Am Chem Soc 1999, 121, 49, 11261. |
| 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) | 11687 | (2R,3R)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetanyl acetate | C13H25NO4Si | 详情 | 详情 | |
| (II) | 31601 | tert-butyl 2-oxobutyl carbonate | C9H16O4 | 详情 | 详情 | |
| (III) | 31602 | tert-butyl (3R)-3-[(2R,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetidinyl]-2-oxobutyl carbonate | C20H37NO6Si | 详情 | 详情 | |
| (IV) | 31603 | tert-butyl (3R)-2-oxo-3-((2R,3S)-4-oxo-3-[(1R)-1-[(triethylsilyl)oxy]ethyl]azetidinyl)butyl carbonate | C20H37NO6Si | 详情 | 详情 | |
| (V) | 31604 | 3-(4-nitrobenzyloxy)-2-oxopropanoyl chloride | C9H6ClNO5 | 详情 | 详情 | |
| (VI) | 31605 | tert-butyl (3R)-3-((2R,3S)-1-[3-(4-nitrobenzyloxy)-2-oxopropanoyl]-4-oxo-3-[(1R)-1-[(triethylsilyl)oxy]ethyl]azetidinyl)-2-oxobutyl carbonate | C29H42N2O11Si | 详情 | 详情 | |
| (VII) | 31606 | tert-butyl ((4S,5R,6S)-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-7-oxo-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-en-3-yl)methyl carbonate | C29H42N2O9Si | 详情 | 详情 | |
| (VIII) | 31607 | 1-(2-amino-2-oxoethyl)-4-[2-(1,1-dioxo-1,2-dihydro-2H-naphtho[1,8-cd]isothiazol-6-yl)ethyl]-1,4-diazoniabicyclo[2.2.2]octane di(trifluoromethanesulfonate) | C22H26F6N4O9S3 | 详情 | 详情 | |
| (IX) | 31160 | 1-[(2R,4S,5R)-4-(benzyloxy)-5-[(trityloxy)methyl]tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | C35H32N2O5 | 详情 | 详情 |