CAS: 21210-43-5; (S)-Methyl 2-Hydroxy-2-Phenylacetate

该化合物是属于甲酸酯类的有机化合物,其特征是其手性,其特征是(S)-抗生素是生物活性形态,该化合物一般看起来无色可粉黄黄色液体或固体,视其纯度和形态而定. 甲基(S--+)-mandelate在乙醇和乙醇等有机溶剂中是可溶解的,但水溶解度有限. 它经常用于合成药物,并因其能影响反应的立体化学而成为有机化学的手制构件. 复合光学活动是手性分子的一个关键特征,允许其旋转飞机极化光. 此外,它可能在不对称合成领域和作为生产各种生物活性化合物的潜在中间体. 处理和储存安全数据,如同任何化学物质一样,都应用于处理和储存.

结构式图片

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上下游产品

methanol phenylglyoxal hydrate (S)-Mandelic acid S)-1-methyl-2-phenyl-ethyl)-amino]-ethanethiol2-[methyl-((S)-1-methyl-2-phenyl-ethyl)-amino]-ethanethiol diethyl ether (R)-1,1,2-triphenylethane-1,2-diol (S)-1-phenyl-1,2-ethanediol (S)-methyl 2-methoxy-2-phenylacetate

合成工艺路线路线简述

    扁桃酸置于daicel Chiralcel Od-3体系中,用 正己烷,异丙醇,仲丁醇 用作溶剂,化学反应生成L-扁桃酸甲酯
    参考文献:C1-C4醇中扁桃酸光学拆分中的手性转换:基于非对映异构体盐的x射线晶体结构阐明溶剂效应
    标题:C1-C4醇中扁桃酸光学拆分中的手性转换:基于非对映异构体盐的x射线晶体结构阐明溶剂效应
    摘要:本文证明了在c1-C4醇中使用(1 R,2 S)-2-氨基-1,2-二苯乙醇(adpe)在扁桃酸(ma)的光学拆分中进行手性转换.从较长的醇溶剂(n-Proh,S-Buoh,I-Buoh和n-Buoh)中将ma盐的非对映混合物重结晶会生成(R)-Ma盐,而(S)-Ma盐则优先由较短的醇溶剂(meoh,Etoh,I-Proh和t-Buoh)沉积.热重分析和11 H NMR光谱表明,所用的所有溶剂均被掺入非对映异构体盐中,并且所掺入的醇的稳定性随其烷基链有效表面积的增加而增加.八个溶剂化非对映异构盐对的x射线晶体结构表明,氢键网络(片状或柱状)的类型和柱状结构的排列受所含醇的长度控制.通过比较两个非对映异构ma盐晶体结构,研究了它们显示手性切换的相对稳定性.
    Doi:10.1021/cg500483P

    海关参考信息

    专利信息


    专利号:US-11370736-B2
    优先权日:2019-04-01
    标 题:Synthesis of fluoro hemiacetals via transition metal-catalyzed fluoro ester and carboxamide hydrogenation
    发明人:DUB PAVEL A; BATRICE RAMI J; GORDON JOHN C
    权利人:TRIAD NAT SECURITY LLC
    摘要:This application is directed to use of transition metal-ligand complexes to hydrogenate fluorinated esters and carboxamides into fluorinated hemiacetals. Methods for synthesis of certain ligands are also provided.

    专利号:US-5399721-A
    优先权日:1990-01-12
    标题:Synthesis of optically pure 4-aryl-2-hydroxytetronic acids
    发明人:HOPPER ALLEN T; WITIAK DONALD T
    权利人:UNIV OHIO STATE RES FOUND
    摘要:The present invention relates to a method for synthesis of optically pure stereogenically labile 4-aryl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase. the invention further relates to the pharmaceutical use of such compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis.

    专利号:US-6384228-B2
    优先权日:1998-05-26
    标题 :Method for synthesis of halopyridyl-azacyclopentane derivative and intermediate thereof
    发明人:NODE MANABU; NAKAMURA DAISAKU; FUJIWARA TOSHIO; ICHIHASHI SHOGO
    权利人:NIHON MEDIPHYSICS CO LTD
    摘要:The present invention relates to a method for synthesis of an optically active halopyridyl-azacyclo-pentane derivative and the intermediate thereof which comprises preparing an optically active allene-1,3-dicarboxylic acid ester derivative from an optically active acetonedicarboxylic acid ester derivative and then proceeding through a 7-azabicyclo[2.2.1]heptane derivative to obtain the objective product.

    专利号:WO-9529150-A1
    优先权日:1994-04-21
    标 题 :Synthesis of prototypes for renin inhibitors
    发明人:HANESSIAN STEPHEN
    权利人:CIBA GEIGY AG; HANESSIAN STEPHEN
    摘要:Prototype renin inhibitors having general structure (I), where n is 0-3 inclusive, A are either both hydrogen atoms or together are a single carbon-nitrogen bond, R1 is hydrogen, or hydrocarbylcarboxy wherein the hydrocarbyl entity is selected from the group consisting of alkyl of 1 to 6 carbon atoms or aralkyl of 7 to 10 carbon atoms, R2 and R3 or independently alkyl of 1 to 4 carbon atoms, R4 is alkyl of 1 to 6 carbon atoms or a substituent of aliphatic character such as, for example, butyl, 2-morpholinoethyl or 2-carbamoyl-2-methyl-propyl, R5 is selected from aromatics, substitued aromatics and heteroaromatics, substituted or unsubstituted cycloalkyls, cycloalkenes having 3 to 8 carbon atoms, with substituents selected from alkyl, alkoxy of 3 to 10 carbon atoms and alkoxy derivatives such as 3-methoxy-propyloxy, primary and secondary amides, alkyl derivatives, are prepared by novel multistep synthesis. Such compounds are valuable intermediates for the manufacture of pharmaceutical such as Renin inhibitors and HIV-protease inhibitors.

    专利号:US-4978744-A
    优先权日:1989-01-27
    标题:Synthesis of dolastatin 10
    发明人:PETTIT GEORGE R; SINGH SHEO B
    权利人:UNIV ARIZONA
    摘要:A complicated but extremely important scheme of synthesis has been developed for synthesizing, dolaisoleuine, dolaproine, dolaphenine and dolavaline from readily available starting materials such as Z-(S,S)isoleucine, S-phenylalaline, S-phenylalaninol, S-prolinol, S-mandelate, and S-valine. The requisite amino acids have been combined using several peptide coupling procedures to create pharmaceutically pure dolastatin 10.

    专利号:US-6469193-B1
    优先权日:1999-02-26
    标 题 :Efficient synthesis of alkyl carbonates
    发明人:JUNG KYUNG WOON
    权利人:UNIV SOUTH FLORIDA
    摘要:Efficient synthetic methods towards mixed aliphatic carbonates through the three component couplings of aliphatic alcohols, alkyl halides and carbon dioxide in the presence of cesium carbonate and tetrabutylammonium iode (TBAI). Due to their enhanced nucleophilicities, cesium alkoxides are smoothly incorporated into CO 2 , allowing for mild reaction conditions such as ambient temperatures and short reaction durations. Various primary and secondary substrates are compatible under the standard conditions, offering high yields, while chiral templates such as α-hydroxy carbonyls are resistant to racemization.
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    合成参考文献


    摘要:Zaidlewicz, M.; Pakulski, M. M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 85.
    摘要:Wu, X.; Xiao, J., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 282.
    摘要:Riva, R.; Banfi, L.; Basso, A., Science of Synthesis: Multicomponent Reactions, (2013) 1, 398.
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