CAS: 101711-78-8; (S)-4-Benzyl-3-Propionyloxazolidin-2-One

该化合物是一个有机的氧化氮素化合物,具有五人环状环状,含有氮和氧原子的氮和氧原子.该化合物的特点是其特定的立体化学特征,以(4S)名称表示,该名称是指其替代体外中心周围的空间安排.一个苯基集团和一个丙基集团的存在有助于其结构复杂性并可能影响其在生物系统中的再活动与互动.奥氧素在医药化学中的应用,特别是作为药物合成的中间体和潜在的抗微生物剂.该化合物的溶性,稳定性和再活性可因诸如pH和温度等环境条件而变化.此外,其气性可能会产生独特的药性特性,使其在对等纯药的研制中具有兴趣.

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欧盟法规

ECHA物质C&L通报

上下游产品

(S)-4-Benzyl-2-oxazolidinone propionyl chloride propionic acid propionic acid anhydride (S)-4-benzyl-3-((R,E)-2-methyl-5-phenylpent-4-enoyl)oxazolidin-2-one (4S,2'R)-3-(3'-(benzyloxy)-2'-methylpropanoyl)-4-benzyl-1,3-oxazolidin-2-one -3--4-benzyl-2-oxazolidinone3(2S,3R)4S-3-3-hydroxy-2-methyl-6-heptenoyl-4-benzyl-2-oxazolidinone -3-(2-Methyl-1-oxo°Ctyl)-4-(phenylmethyl)-2-oxazolidinone3(2'R),4S-3-(2-Methyl-1-oxo°Ctyl)-4-(phenylmethyl)-2-oxazolidinone

合成工艺路线路线简述

    (S)-4-苄基-2-唑烷酮 以 正己烷 用作溶剂,化学反应生成(S)-4-苄基-3-丙酰基-2-噁唑烷酮
    参考文献:Diastereoisomers Of N.Sup.6-Endo-Bicyclo[2.2.1]Heptyladenosine As
    标题:Diastereoisomers Of N.Sup.6-Endo-Bicyclo[2.2.1]Heptyladenosine As
    摘要:(1R-Endo)或(1S-Endo)-N-双环[2.2.1]庚基腺苷及其药用酸盐,具有极具吸引力的降压特性和意外的a.Sub.1和a.Sub.2受体结合活性,其制造过程,制药组合物和使用该化合物和组合物的方法.

    专利信息


    专利号:US-6093812-A
    优先权日:1991-07-23
    标 题 :Process for the stereospecific synthesis of azetidinones
    发明人:THIRUVENGADAM TIRUVETTIPURAM K; TANN CHOU-HONG; LEE JUNNING; MCALLISTER TIMOTHY; COLON CESAR; BARTON DEREK H R; BRESLOW RONALD; SUDHAKAR ANANTHA
    权利人:SCHERING CORP
    摘要:This invention provides an improved process for producing azetidinones. More particularly, this invention provides the steps of producing an trans-azetidinone represented by the formula from a carboxylic acid R2-D-CH2COOH, an aldehyde R1-A-CHO and an amine RNH2, by the steps of: (a1) converting a carboxylic acid to the corresponding acid chloride; (b1) deprotonating a chiral oxazolidinone and treating the resulting anion with the product of step (a1); (c1) enolizing the product of step (b1) and condensing with the aldehyde; (d1) hydrolyzing the product of step (c1); (e1) condensing the product of step (d1) with the amine; and (f1) cyclizing the product of step (e1). Alternatively, the process comprises (a2) enolizing the product of step (b1) and condensing, in the presence of a Lewis acid, with a Schiff's base prepared from the aldehyde and the amine; and (b2) cyclizing the product of step (a2).

    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-7700783-B2
    优先权日:2003-10-09
    标题 :Synthesis of discodermolide and variants thereof
    发明人:SMITH III AMOS B; FREEZE BRIAN SCOTT; XIAN MING
    权利人:UNIV PENNSYLVANIA
    摘要:Processes for synthesizing a compound of Formula (I) are provided by reacting a compound of Formula (i) with a compound of Formula (xx).

    专利号:US-5132457-A
    优先权日:1991-08-26
    标 题 :Stereospecific synthesis of 2(R)-2-methyl-3-dimethylamino-propiophenone (d-DAMP)
    发明人:MATHEW JACOB
    权利人:MALLINCKRODT SPEC CHEM
    摘要:In a method for producing 2(R)-2-methyl-3-dimethylamino-propiophenone (d-DAMP), a chiral ester of the formula ##STR1## wherein R is an alkyl of from 1 to about 5 carbon atoms, is provided. The chiral easter of formula (I) is converted into a chiral amino-alcohol of the formula ##STR2## and the chiral amino-alcohol is oxidized so as to form d-DAMP.

    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.
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    合成参考文献


    摘要:Yliniemelä-Sipari, S. M.; Pihko, P. M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 625.
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