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【结 构 式】

【分子编号】52175

【品名】(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5R,6S)-6-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-7-oxo-3-[(2R)tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C23H33NO8SSi

【 分 子 量 】511.66846

【元素组成】C 53.99% H 6.5% N 2.74% O 25.02% S 6.27% Si 5.49%

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:(XXIX)

Treatment of 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one (XXII) with potassium formate (XXIII) by means of KI and NaHCO3 in DMF affords the formyloxymethyl derivative (XXIV), which is converted into the hydroxymethyl derivative (XXV) by refluxing in MeOH. Coupling of compound (XXV) with oxalyl chloride (XXVI) in dichloromethane furnishes compound (XXVII), which is then condensed with protected azetidinone (VI) by means of Et3N in dichloromethane to yield compound (XXVIII). Intramolecular Wittig cyclization of compound (XXVIII) by means of triethyl phosphite in refluxing xylene provides the silylated faropenem daloxate (XXIX), which is finally deprotected by means of either Et3N tris(hydrogen fluoride) in ethyl acetate or tetrabutylammonium fluoride (TBAF) and AcOH in THF.

1 Rabasseda, X.; Sorbera, L.A.; del Fresno, M.; Castaner, J.; Faropenem daloxate. Drugs Fut 2002, 27, 3, 223.
2 Ishiguro, M.; Kanebo, A.; Kaku, T.; Nakatsuka, T. (Nippon Soda Co., Ltd.; Suntory Ltd.); Method of desilylating silylether cpds.. EP 0612749 .
3 Fukami, H.; Shima, K.; Nakatsuka, T.; Iwata, H.; Yoshida, T.; Mizukawa, Y.; Shibata, M.; Sekiuchi, K.; Iwanami, T. (Suntory Ltd.); Preparation method of penem derivs.. JP 1994192270 .
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) 11689 S-[(2R,3S)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetanyl] (2R)tetrahydro-2-furancarbothioate C16H29NO4SSi 详情 详情
(XXII) 16911 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one C5H5ClO3 详情 详情
(XXIII) 52172 Potassium formate; Formic acid potassium salt 590-29-4 CHKO2 详情 详情
(XXIV) 50467 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl formate C6H6O5 详情 详情
(XXV) 50468 4-(hydroxymethyl)-5-methyl-1,3-dioxol-2-one C5H6O4 详情 详情
(XXVI) 29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(XXVII) 52173 2-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy]-2-oxoacetyl chloride C7H5ClO6 详情 详情
(XXVIII) 52174 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-((3S,4R)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-2-oxo-4-[[(2R)tetrahydro-2-furanylcarbonyl]sulfanyl]azetidinyl)-2-oxoacetate C23H33NO10SSi 详情 详情
(XXIX) 52175 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5R,6S)-6-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-7-oxo-3-[(2R)tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C23H33NO8SSi 详情 详情
Extended Information