CAS: 136561-53-0; (2R,3S)-3-Amino-2-Hydroxy-3-Phenylpropanoic Acid

该化合物是一种非蛋白性非蛋白性氨基酸衍生物,在有机合成和制药应用方面有很大的用途,其立体化学定义结构包括(2R)和(3S)配置,使它成为培养生物活性化合物,包括基于税制的抗癌剂的宝贵中间体.3级苯基组在不对称合成中增强了其多功能性,能够准确控制立体化学结果.该化合物因其坚固的骨干和功能性组的兼容性,对建造复杂的分子结构特别有利.高纯度和精美的立体化学学确保研究和工业过程的再生,使其成为医药化学和药物开发的首选.

结构式图片

相似化合物

132201-32-2 132201-32-2 6049-55-4

上下游产品

2-chloro-3-hydroxy-3-phenyl-propionic acid 2-hydroxy-3-amino-3-phenylpropionamide RS,3SR)-2,3-epoxy-3-phenyl-propionic acid(2RS,3SR)-2,3-epoxy-3-phenyl-propionic acid (+/-)-anti-3-amino-2-hydroxy-3-phenylpropanamide *,3R*)-3-phenyl-3-amino-2-hydroxypropanoate hydr°Chlorideethyl (2R*,3R*)-3-phenyl-3-amino-2-hydroxypropanoate hydr°Chloride benzaldehyde phenylglycin (2R,3S)-N-benzoyl-3-phenylisoserine

合成工艺路线路线简述

    2-Hydroxy-3-(4-Methyl Benzenesulfonylamino)-3-Phenyl-Propionic Acid Methyl Ester置于氢溴酸,苯酚体系中,用 溶剂黄146 用作溶剂,化学反应 12.0H,以77%的收率获得(2R,3S)-3-苯基异丝氨酸
    参考文献:Catalytic Asymmetric Aminohydroxylation Provides A Short Taxol Side-Chain Synthesis.
    标题:Catalytic Asymmetric Aminohydroxylation Provides A Short Taxol Side-Chain Synthesis.
    摘要:The P-Toluenesulfonamide Derivative Of The C-13 Side-Chain Of Taxol Was Prepared On A One Third Mole Scale In A Single Step From Methyl Cinnamate. The Process Employed Is Catalytic Asymmetric Aminohydroxylation (Catalytic Aa). In The Present Case,There Is No Work-Up Other Than Filtration Of The Pure Product Which Is Insoluble In The Reaction Mixture. The Sulfonamide Protecting Group Is Removed By Acidic Hydrolysis.
    Doi:10.3891/acta.Chem.Scand.50-0649

    海关参考信息

    专利信息


    专利号:US-2009306400-A1
    优先权日:2006-03-27
    标 题:Convergent process for the synthesis of taxane derivatives.
    发明人:HENRI JOHN T; MCCHESNEY JAMES D; VENKATARAMAN SYLESH K; LAMB RODGER L; FOSTER JONATHAN E; SUMNER CHRISTIAN M; YE SHANGPING
    权利人:HENRI JOHN T; MCCHESNEY JAMES D; VENKATARAMAN SYLESH K; LAMB RODGER L; FOSTER JONATHAN E; SUMNER CHRISTIAN M; YE SHANGPING
    摘要:The present invention is broadly directed to novel compounds useful for the synthesis of biologically active compounds, including taxane derivatives, and convergent processes for the preparation of these taxane derivatives and their intermediates.

    专利号:US-5675025-A
    优先权日:1995-06-07
    标题:Paclitaxel synthesis from precursor compounds and methods of producing the same
    发明人:SISTI NICHOLAS J; SWINDELL CHARLES S; CHANDER MADHAVI C
    权利人:NAPRO BIOTHERAPEUTICS INC
    摘要:An efficient protocol for the synthesis of taxol, taxol analogs and their intermediates is described. The process includes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, celphalomanninne and various analogs, including photoaffinity labeling candidates.

    专利号:US-5948919-A
    优先权日:1993-02-05
    标题:Paclitaxel synthesis from precursor compounds and methods of producing the same
    发明人:SISTI NICHOLAS J; SWINDELL CHARLES S; CHANDER MADHAVI C
    权利人:NAPRO BIOTHERAPEUTICS INC; BRYN MAWR COLLEGE
    摘要:An efficient protocol for the synthesis of taxol, taxol analogs and their intermediates is described. The process incudes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, celphalomanninne and various analogs, including photoaffinity labeling candidates.

    专利号:US-6509506-B1
    优先权日:1997-05-21
    标 题 :Two step synthesis of D- and L- α-amino acids and D- and L- α-amino aldehydes
    发明人:SHARPLESS K BARRY; LI GUIGEN
    权利人:SCRIPPS RESEARCH INST
    摘要:D- and L- α-amino acids and D- and L-α-amino aldehydes are synthesized from olefin substrates in two steps. The first step is a catalyzed asymmetric aminohydroxylation addition reaction to the olefin substrate. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantioselectively, divalent ligands are preferred over monovalent ligands because of their enhanced regio-and enantio-selectivity. As an oxidant nitrogen source for the addition reaction, either a carbamate or sulfonamide may be employed. If carbamate is employed as an oxidant nitrogen source, the resultant β-hydoxycarbamate is deprotected to yield the corresponding β-hydroxyamine. If sulfonamide is employed as an oxidant nitrogen source, the resultant β-hydroxysulfonamide is deprotected to yield the corresponding β-hydroxyamine. The resultant β-hydroxyamine is then selectively oxidized in a second synthetic step to produce the desired D- and L- α-amino acid or D- and L-α-amino aldehyde.

    专利号:US-2012071674-A1
    优先权日:2009-05-29
    标 题:Solvates of docetaxel
    发明人:CIESLINSKI WITOLD STANISLAW
    权利人:CIESLINSKI WITOLD STANISLAW; PRZED PROD WDROZENIOWE IFOTAM SP Z O O
    摘要:The present invention provides solvates of 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1,7β,10β-trihydroxy-9-oxo-tax-11-en-13α-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate and C2-3-alkyl esters of formic acid, process of their preparation and their use in the synthesis of the pharmaceutically pure 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1,7β,10β-trihydroxy-9-oxo-tax-11-en-13α-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate.

    专利号:US-2004110228-A1
    优先权日:2002-04-01
    标 题:Combinatorial organic synthesis of unique biologically active compounds
    发明人:MCALPINE SHELLI R; TAYLOR RACHEL E; BOLLA MEGAN L; SEGALL ANCA M
    摘要:The invention provides a method for making a combinatorial library of cyclic compounds, such as Holliday junction-trapping compounds, comprising the steps of (a) obtaining a plurality of trimers according to the generic structure X 1- X 2- X 3 , wherein X 1 , X 2 and X 3 can be independently any naturally or nonnaturally occurring amino acids or peptidomimetics thereof; (b) optionally coupling a spacer S to the trimer at either end; (c) cyclizing two trimers or trimer-spacer conjugates in a head-to-tail orientation; thereby obtaining a combinatorial library of compounds, wherein the library does not include an unmodifed or naturally occurring Holliday Junction-trapping compounds. The invention additionally provides methods macrocyclic compounds that are synergimycin derivatives.
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    合成参考文献


    参考文献:10.1055/s-2006-958957
    摘要:Petrini M, Torregiani E. Recent Advances in Stereoselective Syntheses Using N-Acylimines. Synthesis. 2007 Jan;2007(2):159–86. doi: 10.1055/s-2006-958957.
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