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【结 构 式】

【分子编号】30161

【品名】1-(2-amino-2-oxoethyl)-4-[2-[2-([(4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-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]-1,4-diazoniabicyclo[2.2.2

【CA登记号】

【 分 子 式 】C39H44ClF3N6O12S2

【 分 子 量 】945.3915096

【元素组成】C 49.55% H 4.69% Cl 3.75% F 6.03% N 8.89% O 20.31% S 6.78%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(L)

Coupling of carbapenem (XLII) with sultam (VIIIb) under Mitsunobu conditions gave adduct (XLVII), which was desylilated to yield alcohol (XLVIII). Formation of the corresponding triflate, followed by condensation with bicyclic compound (XLV) provided (II), which was converted to (L) upon treatment with HCl and NaCl. The p-nitrobenzyl ester of (L) was finally deprotected by hydrogenation over Pd/C to provide the title carboxylic acid. A further procedure to obtain the target compound is to repeat the described synthesis but using carbapenem (XXXVII), instead of carbapenem (XLII).

1 Yasuda, N.; et al.; Preparation of anti-MRS carbapenem L-786,392. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-31.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIIIb) 30125 6-[2-[(triethylsilyl)oxy]ethyl]-2H-naphtho[1,8-cd]isothiazole-1,1(2H)-dione C18H25NO3SSi 详情 详情
(IL) 30160 1-(2-amino-2-oxoethyl)-4-(2-[2-[((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]-1,1-dioxo-1,2-dihydro-2H-naphtho[1,8-cd]isothiazol-6-yl]ethyl)-1,4-diazonia C46H58F6N6O15S3Si 详情 详情
(XLII) 30154 (4S,5R,6S)-3-(hydroxymethyl)-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-en-7-one C24H34N2O7Si 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
(XLVII) 30158 2-[((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]-6-[2-[(triethylsilyl)oxy]ethyl]-2H-naphtho[1,8-cd]isothiazole-1,1(2H)-dione C42H57N3O9SSi2 详情 详情
(XLVIII) 30159 6-(2-hydroxyethyl)-2-[((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]-2H-naphtho[1,8-cd]isothiazole-1,1(2H)-dione C36H43N3O9SSi 详情 详情
(L) 30161 1-(2-amino-2-oxoethyl)-4-[2-[2-([(4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-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]-1,4-diazoniabicyclo[2.2.2 C39H44ClF3N6O12S2 详情 详情
Extended Information