CAS: 36567-72-3; (S)-3-Hydroxy-3-Phenylpropanoic Acid

上下游产品

CAS号614-20-0 苯甲酰乙酸 | CAS号614-16-4 苯甲酰乙腈 | CAS号1375257-32-1 (S)-3-[(S)-3-hy... | CAS号1407186-17-7 (S)-3-(3-phenyl... | CAS号104672-27-7 (3'S,4S)-3-(3'-... | CAS号1338045-88-7 (S)-2,6-dimetho... | CAS号100-52-7 苯甲醛 | CAS号5764-85-2 3-羟基-3-苯基丙酸乙酯 | CAS号77815-27-1 1-[1-(4-toluens... | CAS号33401-74-0 (S)-3-羟基-3-苯基丙酸乙酯 | CAS号36615-45-9 (S)-3-羟基-3-苯基丙酸甲酯 | CAS号96854-34-1 (S)-1-苯基-1,3-丙二醇 | CAS号621-82-9 肉桂酸 | CAS号15463-91-9 Beta-溴苯丙酸

📜苯甲酰乙腈置于葡萄糖,D-Glucose Dehydrogenase,Alcohol Dehydrogenase Ymr226C From Saccharomyces Cerevisiae,还原型辅酶ii(Nadph)四钠盐,Nitrilase From Bradyrhizobium Japonicum Strain Usda110体系中,用 二甲基亚砜 用作溶剂,化学反应 72.0H,以92%的收率获得(S)-3-羟基-3-苯基丙酸
参考文献:通过酶促还原或顺序还原/水解反应不对称合成β-羟基腈和β-羟基羧酸的对映体
标题:通过酶促还原或顺序还原/水解反应不对称合成β-羟基腈和β-羟基羧酸的对映体
摘要:使用分离的羰基还原酶还原芳香族β-酮腈可完全消除竞争性α-乙基化,这在全细胞生物催化剂中通常会观测到.通过选择合适的重组羰基还原酶,β-酮腈的还原得到(R)-或(S)-β-羟基腈,具有优异的光学纯度和收率.随后,所获得的光学纯的β-羟基腈的腈水解酶催化水解以高收率产生了相应的β-羟基羧酸.更重要的是,连续的酶促还原和水解反应可以"两步一锅"的方式进行,而无需分离中间体β-羟基腈,从而降低了成本并将对环境的影响降至最低.这使得可以以优异的光学纯度容易地获得具有药学重要性的手性β-羟基腈和β-羟基羧酸的对映体.
Doi:10.1021/jo802495F

专利信息

专利号:US-4921798-A
优先权日:1989-09-25
标题 :Synthesis of (aryl or arylalkyl)-3-hydroxy propionic acids and aryl alkanediols having high optical purity
发明人：BOAZ NEIL W
权利人:EASTMAN KODAK CO
摘要:R- and S-1-Phenyl-1,3-propanediol, each of high optical purity, were prepared by a chemoenzymatic sequence starting with ethyl benzoylacetate. The first step was a catalytic hydrogenation of the β-ketoester conducted at room temperature. The enzymatic hydrolysis of the resulting hydroxyester proceeded in a facile manner using a commercial preparation of the lipase from Pseudomonas fluorescens. The enzymatic hydrolysis proceeded at a moderate rate (350 mg lipase/0.10 mol of racemic ester required a 20-hour reaction time with an enantiomeric rate ratio (E value) of 36). The hydrolysis was run to 45-50% conversion to afford isolated S-3-phenyl-3-hydroxypropionic acid of 85-90% ee after separation from the residual ester (aqueous base extraction). The optical purity of the hydroxy acid was determined by conversion to the methyl ester (CH 3 I, KHCO 3 , acetone), and derivatization with S-MTPA-Cl, and 1 H NMR analysis. A single recrystallization of the isolated acid afforded optically pure (>98% ee) S-3-phenyl-3-hydroxypropionic acid in an overall 36% yield from the racemic ester. The acid was reduced with borane in THF to afford optically purs S-diol in 97% yield after crystallization. The overall sequence proceeded in 34% total yield from racemic ester with an additional 45-55% recovered as the antipodal ester. This antipodal ester is obtained in 85-95% ee, and the corresponding hydroxy-acid was readily obtained (NaOH), CH 3 OH/H 2 O) and recrystallized to optical purity. Reduction then afforded R-1-phenyl-1,3-propanediol in 30% to overall yield from racemic ester.

专利号:US-6303796-B1
优先权日:1998-02-26
标题:β-diketone compounds β-diketone compounds coordinated to metal, method of organic synthesis with these, and catalyst
发明人：YAMAGUCHI MASAHIKO; SATO MASAYUKI
权利人:CHISSO CORP
摘要:The present invention provides a novel β-diketone compound represented by formula (3): n [wherein X represents (CH 2 ) n ; n represents an integer of 2-20; and the CH 2 of X may be replaced by an oxygen atom, a hetero ring, or an aromatic ring, but oxygen atoms are not sequentially arranged in X], and a metal-coordinated β-diketone compound in which a metal is coordinated with the β-diketone compound. The compound of the present invention can be easily synthesized, and serves as a catalyst for asymmetric synthesis which can provide high asymmetric yield and chemical yield.

专利号:WO-9104334-A1
优先权日:1989-09-25
标题 :Synthesis of aryl alkanediols having high optical purity

专利号:EP-0494203-B1
优先权日:1989-09-25
标 题:Synthesis of aryl alkanediols having high optical purity

专利号:US-2010267100-A1
优先权日:2007-03-21
标 题:Enzymatic synthesis of optically pure beta-hydroxy carboxylic acids and their derivatives
发明人：HUA LING; ZHU DUNMING; MUKHERJEE CHANDRANI; BIEHL EDWARD R
权利人:HUA LING; ZHU DUNMING; MUKHERJEE CHANDRANI; BIEHL EDWARD R
摘要:The present disclosure is related to systems, compositions, and methods for producing a β-hydroxy carboxylic acid and/or a β-hydroxy carboxylic amide in enantiomeric excess (e.g., enantiomerically pure). In some specific example embodiments, a method may include contacting a substrate and/or intermediate with a cyanide, a ketoreductase, a nitrilase, and/or a nitrile hydratase. Systems, compositions, and methods, in some embodiments, may produce a β-hydroxy carboxylic acid and/or a β-hydroxy carboxylic amide in enantiomeric excess under convenient conditions (e.g., pH 5-9 and temperatures under 50° C.).

专利号:EP-1067127-A1
优先权日:1998-02-26
标题:Novel beta-diketone compounds, beta-diketone compounds coordinated to metal, method of organic synthesis with these, and catalyst