CAS: 90776-58-2; (R)-2-((2S,3S)-3-((R)-1-((Tert-Butyldimethylsilyl)Oxy)Ethyl)-4-Oxoazetidin-2-yl)Propanoic Acid

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CAS号76899-07-5 (3R,4R)-4-aceto...

[(2R,3R)-3-[1-[tert-Butyl(Dimethyl)Silyl]Oxyethyl]-4-Oxo-1-Trimethylsilylazetidin-2-Yl] Acetate置于三氟甲磺酸三甲基硅酯 Sodium Hydroxide体系中,用 甲醇,二氯甲烷 作为反应溶剂,化学反应生成 (S)-2-((2R,3S)-3-((R)-1-((叔丁基二甲基甲硅烷基)氧基)乙基)-4-氧代氮杂环丁烷-2-基)丙酸
参考文献:1-取代的碳青霉烯类抗生素的合成研究
标题:1-取代的碳青霉烯类抗生素的合成研究
摘要:描述了1-取代的碳青霉烯的全合成.关键步骤是乙酰氧基氮杂环丁酮(7)与乙烯酮甲硅烷基缩醛(8)的反应.
DOI:10.1016/s0040-4039(00)94938-4

专利信息

专利号:US-4895939-A
优先权日:1986-02-24
标题:High percentage β-yield synthesis of carbapenem intermediates
发明人：MARTEL ALAIN; DARIS JEAN-PAUL; CORBEIL JACQUES
权利人:BRISTOL MYERS CO
摘要:Disclosed herein is a novel high beta -yield producing novel intermediates of the formula where R4 is useful in the synthesis of 1- beta -alkyl carbapenems.

专利号:US-6340751-B1
优先权日:1998-07-24
标 题 :Process for the preparation of 4-substituted azetidinone derivatives
发明人：SAITO TAKAO; MURAYAMA TOSHIYUKI; MATSUMOTO TAKAJI; MIURA TAKASHI
权利人:TAKASAGO PERFUMERY CO LTD
摘要:Disclosed is a process for the preparation of a 4-substituted azetidinone derivative, which comprises reacting an azetidinone derivative and an amide compound in the presence of a magnesium compound such as those represented by the following formulas (II): n and (IV): n represented by the following formula (III): n n n MgR 5 R 6   (III) n n n wherein R 5 represents a C 1-12 alkyl group, a C 2-5 alkenyl group, a 5- to 8-membered alicyclic group which may be substituted by a lower C 1-4 alkyl group, a phenyl group which may be substituted by a lower C 1-4 alkyl group, a lower C 1-4 alkoxy group or a halogen atom or a benzyl group which may be substituted by a lower C 1-4 alkyl group, a lower C 1-4 alkoxy group or a halogen atom, and R 6 represents a halogen atom, a methanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group, an acetoxy group which may be substituted by a halogen atom or a cyano group or an OR 7 group (R 7 representing a lower C 1-4 alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group). The process provides an industrially excellent process for the preparation of a 4-substituted azetidinone derivative which permits the selective preparation of an intermediate for the synthesis of a carbapenem antibacterial agent having a desired 1-β′ configuration.

专利号:US-4772683-A
优先权日:1986-02-24
标 题:High percentage beta-yield synthesis of carbapenem intermediates
发明人：MARTEL ALAIN; DARIS JEAN-PAUL; CORBEIL JACQUES
权利人:BRISTOL MYERS CO
摘要:Disclosed herein is a novel process using novel silyl enol ether intermediates of the formula 8 to generate novel azetidione thiolester intermediates of the formula 12 which can be used to form 1- beta -alkyl carbapenem antibiotics. It has now been discovered that if the R4 group is selected from a small group of moieties having the formula: an increased beta -yield of up to approximately 100% can be obtained.

专利号:US-2011144326-A1
优先权日:2009-12-10
标题:Method for manufacturing stereoselective preparation of 4-BMA using a chiral auxiliary and chiral auxiliary
发明人：TSENG WEI-HONG; CHUANG SHIUAN-TING; HUNG ZUN-YUAN; WU CHING-I
权利人:TSENG WEI-HONG; CHUANG SHIUAN-TING; HUNG ZUN-YUAN; WU CHING-I
摘要:The present invention relates to a process for preparing (3R,4S)-3-[[[R]-1′-t-butyldimethylsilyloxy]ethyl]-4-[(R)-1″-carboxyethyl]-2-azetidinone (beta-methylazetidin-2-one; 4-BMA), a key intermediate for the synthesis of carbapenem and penem antibiotics. Specifically, the present invention relates to a process comprising first, the preparation of a chiral auxiliary from cheap L-Phenylalaninol, and then the preparation of 4-BMA in high yield and high selectivity, under industrially mild condition.

专利号:EP-2345645-A1
优先权日:2009-12-22
标题 :Method for manufacturing stereoselective preparation of 4-bma using a chiral auxiliary and chiral auxiliary
发明人：TSENG WEI-HONG; CHUANG SHIUAN-TING; HUNG ZUN-YUAN; WU CHING-I
权利人:SAVIOR LIFETEC CORP
摘要:The present invention relates to a process for preparing (3R,4S)-3- [[[R]-1 ' -t-butyldimethylsilyloxy ]ethyl]-4-[(R)-1 '-carboxyethyl]-2-azetidinone (beta- methylazetidin-2-one; 4-BMA), a key intermediate for the synthesis of carbapenem and penem antibiotics. Specifically, the present invention relates to a process comprising first, the preparation of a chiral auxiliary from cheap L-Phenylalaninol, and then the preparation of 4-BMA in high yield and high selectivity, under industrially mild condition.

专利号:US-7482445-B2
优先权日:2003-06-18
标 题:Crystalline carbapenem intermediate
发明人：AIHARA KAZUHIRO; HASEGAWA TOSHIFUMI; KITAHARA SHINICHI; WATANABE TAKASHI; ANDO TAKASHI; SAWABE TAKEHIKO; SHITARA EIKI; ATSUMI KUNIO; OTA KAZUMI
权利人:MEIJI SEIKA KAISHA
摘要:This invention relates to crystals of compounds of formula (I), wherein TBS represents t-butyldimethylsilyl, and Ph represents phenyl, or its salt or solvate. Compounds of formula (I) are synthesis intermediates of 2-substituted-1β-methyl carbapenem compounds useful as antimicrobial agents. The crystals of the present invention have excellent handleability and can realize the production of carbapenem compounds having excellent antimicrobial activity in a simpler manner with improved yield and purity.