CAS: 17609-52-8; (R)-2-(((Benzyloxy)Carbonyl)Amino)-2-Phenylacetic Acid

该化合物是一种在peptide合成和制药研究中广泛使用的非蛋白性非蛋白性氨酸衍生物,其主要优点包括高对映性纯度,这对药物开发和不对称合成中的立体选择性应用很有价值.苯氧基碳基(Z)保护组在混合反应期间增强了稳定性,同时在温和条件下仍可选择性地重新移动.该化合物是建造结构多样的peptides和生物活性分子的多用途建筑构件.其硬性苯丙烯骨干有助于目标化合物的符合性限制,提高结合性和代谢稳定性.Z-D-Phg-OH在药用化学中特别有用,用于开发ptiomic和酶抑制剂.

结构式图片

相似化合物

53990-33-3 102410-65-1 111524-95-9

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合成工艺路线路线简述

    2-氨基-2-苯基乙酸置于四(三苯基膦)钯 吗啉,N-甲基吗啉,Hydroquinidine Anthraquinone-1,4-Diyl Diether,4 A Molecular Sieve体系中,用 四氢呋喃,乙醚 用作溶剂,化学反应 4.17H,反应生成苄氧羰酰基苯甘氨酸
    参考文献:快速,室温动态动力学分辨率的发展,以有效地不对称合成α-芳基氨基酸.
    标题:快速,室温动态动力学分辨率的发展,以有效地不对称合成α-芳基氨基酸.
    摘要:[反应:见正文]在室温下,外消旋α-芳基unca具有双功能催化修饰金鸡纳生物碱的快速,高效和一般动态动力学拆分(dkr).该dkr导致了高度对映选择性催化方法的发展,该方法可用于实际合成范围广泛的α-芳基和α-杂芳基氨基酸,Ee含量为89-92%,外消旋unca的收率为86-95%.
    Doi:10.1021/ol026660L

    海关参考信息

    专利信息


    专利号:US-3732199-A
    优先权日:1971-03-15
    标 题 :Peptide synthesis
    发明人:SCHWARZ J
    权利人:SQUIBB & SONS INC
    摘要:IMPROVEMENT IN THE SYNTHESIS OF PEPTIDES INVOLVING THE FORMATION OF NOVEL ACTIVE INTERMEDIATES. THESE ACTIVE INTERMEDIATES ARE FORMED BY REACTION AT LOWERED TEMPERATRES OF AN IMIDYL HALIDE WITH THE TERTIARY AMMONIUM SALT OF THE ACID MOIETY OF AN AMINO ACID OR PEPTIDE. THE INTERMEDIATE THUS FORMED IS THEN REACTED WITH THE AMINO MOIETY OF THE AMINO ACID OR PEPTIDE TO BE COUPLED, THUS FORMING THE DESIRED PEPTIDE OR POLYPEPTIDE.

    专利号:US-4271172-A
    优先权日:1979-06-25
    标 题 :6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acids, antibacterial compositions thereof and method of use thereof
    发明人:RODRIGUEZ LUDOVIC; LECLERCQ JACQUES; YKMAN PIERRE; COSSEMENT ERIC
    权利人:UCB SA
    摘要:6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acids, salts and esters thereof of the formula ##STR1## wherein R 1 is hydrogen, benzyl or an alkali metal or ammonium ion and R 2 is methyl, phenyl or benzyl and process for preparing the same. n These compounds are useful as intermediates in the synthesis of a new group of antibiotics having properties similar to penicillins, besides own antibiotic activity with a broad antibacterial spectrum. Therefore, they are useful as antibacterials agents and as therapeutic agents for humans and for animals in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria.

    专利号:US-4171439-A
    优先权日:1975-04-11
    标 题 :Antibacterial analogs of isocephalosporins
    发明人:CONWAY TERRY T; LIM GARY M F; MENARD MARCEL
    权利人:BRISTOL MYERS CO
    摘要:There is described the stereoselective total synthesis of novel DELTA 2,3-1,4-morpholine-2-carboxylic acids possessing a fused beta -lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula I wherein Z is halo or hydroxyl and X is acylamino. Also included in the invention are compounds of the above formula in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds. The compounds are potent antibacterial agents.

    专利号:US-4112230-A
    优先权日:1975-04-11
    标题 :Δ2,3 -1,4 Morpholine-2-carboxylic acid derivatives as antibacterial agents
    发明人:MENARD MARCEL; LIM GARY M F; CONWAY TERRY T
    权利人:BRISTOL MYERS CO
    摘要:There is described the stereoselective total synthesis of novel DELTA 2,3-1,4-morpholine-2-carboxylic acids possessing a fused beta -lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula I wherein Z is halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.

    专利号:US-4166906-A
    优先权日:1975-04-11
    标题:0-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
    发明人:CONWAY TERRY T; LIM GARY M F; MENARD MARCEL
    权利人:BRISTOL MYERS CO
    摘要:There is described the stereoselective total synthesis of novel DELTA 2,3-1,4-morpholine-2-carboxylic acids possessing a fused beta -lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula I wherein Z is hydroxyl esterified with a sulfonic acid residue and X is acylamino. Also included in the invention are compounds of the above formula in which the carboxyl group of the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds. The compounds are potent antibacterial agents.

    专利号:US-3994883-A
    优先权日:1972-12-27
    标 题 :Penicillin and cephalosporin intermediates
    发明人:BORREVANG POUL; GUDDAL ERLING; PETERSEN HENNING BORGE; FAARUP PETER; NIELSEN JORGEN ILUM
    权利人:NOVO INDUSTRI AS
    摘要:Novel penicillin and cephalosporin intermediates for the synthesis of 6-APA or 7-aminocephem compounds involving formation of a 6 or 7 phosphite amido compound and the conversion of such compound to a desired 6-APA or 7-aminocephem compound.
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    主要参考文献

    [参考文献]: Frycák P, Et Al. High Throughput Multiplexed Method For Evaluation Of Enantioselective Performance Of Chiral Selectors By Hplc-Esi-Ms And Dynamic Titration: Cinchona Alkaloid Carbamates Discriminating N-Blocked Amino Acids. Chirality. 2009 Nov;21(10):929-36.

    合成参考文献


    摘要:Mourad, A. K.; Czekelius, C., Science of Synthesis Knowledge Updates, (2011) 3, 59.
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