CAS: 5445-44-3; O-Benzyl-Dl-Serine

该化合物是一种合成氨基酸衍生物,广泛用于peptide合成和制药研究,其主要优势在于苯基保护的氢氧基组,该组增强了化学反应期间的稳定性,同时允许在受控制条件下有选择地取消保护.该化合物是改变peptide结构的多用途构件,特别是在开发生物活性分子和药物候选物方面.种族(DL)形式为立体化学应用提供了灵活性,使其对研究和工业规模合成都有用.它与标准的peptide联剂和固相合成议定书的兼容性进一步强调了其在有机和药用化学工作流程中的实用性.

结构式图片

上下游产品

CAS号86522-28-3 benzyl 3-benzyl... | CAS号86522-27-2 benzyl 3-benzyl... | CAS号100-51-6 苯甲醇 | CAS号4726-96-9 O-苄基-L-丝氨酸 | CAS号10433-52-0 O-苄基-D-丝氨酸 | CAS号302-84-1 DL-丝氨酸 | CAS号20806-43-3 Cbz-O-苄基-L-丝氨酸 | CAS号5513-74-6 for-ser(bzl)-oh

合成工艺路线路线简述

    2-Azido-3-Benzyloxy-Propionic Acid-Benzyl Ester置于palladium On Activated Charcoal 氢气体系中,用 乙醇 作为反应溶剂,化学反应 8.0H,以79%的收率获得产物o-苄基-Dl-丝氨酸
    参考文献:氨基酸; 13:由α-卤代丙烯酸衍生物合成dl-丝氨酸的研究
    标题:氨基酸; 13:由α-卤代丙烯酸衍生物合成dl-丝氨酸的研究
    摘要:在-35oc下由醇盐催化的醇2加到α-氯丙烯腈(1)中,反应生成3-烷氧基-2-氯丙烷腈3; 在0-5oc下用过量的2-烷基3-烷氧基-2-氯丙酰胺化物4得到.3或4的收率随醇2的pk A值的增加而降低.在碱催化的苯酚5至1的加成反应中,建立了随温度变化的加成平衡,其中平衡位置向有利位置转移. Pk A增加的附加产品6,其值为5.易于水解的4的3-烷氧基-2-氯丙酸酯8.在相转移催化剂的存在下,与叠氮化钠平稳反应,得到3-烷氧基-2-叠氮丙酸酯10.由2-Az1Do-3-苄氧基丙酸苄酯(10B),Dl-丝氨酸(14),Dl-丝氨酸盐酸盐(14.hcl),Dl-丝氨酸甲酯盐酸盐(13A.hcl),0-通过改变氢化条件,可以得到苄基-Dl-丝氨酸(12B)和0-苄基-Dl-丝氨酸苄基酯盐酸盐(11B.hcl).
    DOI:10.1016/s0040-4020(01)86062-2

    海关参考信息

    专利信息


    专利号:US-2022098155-A1
    优先权日:2018-11-14
    标 题 :Novel pathway for the synthesis of diazirines, that may or may not be enriched in nitrogen-15
    发明人:REBOUL VINCENT; FRANCK XAVIER; GLACHET THOMAS; MARZAG HAMID
    权利人:UNIV ROUEN NORMANDIE; UNIV CAEN; INSTITUT NAT DES SCIENCES APPLIQUEES DE ROUEN INSA; CENTRE NAT RECH SCIENT; ECOLE NAT SUPERIEURE DINGENIEURS DE CAEN
    摘要:The present invention concerns a novel method for synthesising diazirines, that may or may not be enriched in nitro-gen-15, from amino acids or imines, via a one-pot synthesis method, comprising the reaction of the starting amino acid or imine with ammonia, which may or may not be enriched in nitrogen-15, and a hypervalent iodine oxidant. The present invention also relates to a method for synthesising ammonia enriched in nitrogen-15. The invention also concerns certain diazirines of formula (I) likely to be obtained by the claimed synthesis method, and also refers to the 15 N 2 -diazirines of formula (I′). The claimed diazirines can be used in photoaffinity labelling. The 15 N 2 -diazirines can also be used in hyperpolarisation, in particular in the medical imaging field.

    专利号:US-6867202-B1
    优先权日:1997-06-25
    标 题 :Treatment of insulin resistance
    发明人:CARPINO PHILIP ALBERT; CHIU CHARLES KWOK-FUNG; PAN LYDIA CODETTA; LEFKER BRUCE ALLEN; TREADWAY JUDITH LEE; ZAWISTOSKI MICHAEL PAUL
    权利人:PFIZER
    摘要:This invention is directed to methods of treating insulin resistance in a mammal which comprise administering an effective amount of a compound of formula I, n n nwhere the variables are defined in the specification, or the stereoisomeric mixtures, diastereomerically enriched, diastereomerically pure, enantiomerically enriched or enantiomerically pure isomers, or the pharmaceutically acceptable salts and prodrugs thereof to said mammal. The compounds of formula I are growth hormone secretagogues and as such are useful for increasing the level of endogenous growth hormone. In another aspect this invention provides certain intermediates which are useful in the synthesis of the foregoing compounds and certain processes useful for the synthesis of said intermediates and th compounds of formula I. This invention is further directed to methods comprising administering to a human or other animal a combination of a functional somatostatin antagonist such as an alpha-2 adrenergic agonist and a compound of formula I.

    专利号:US-2022243244-A1
    优先权日:2019-10-10
    标 题 :Compositions and methods for in vivo synthesis of unnatural polypeptides
    发明人:ROMESBERG FLOYD E; FISCHER EMIL C; HASHIMOTO KOJI; FELDMAN AARON W; DIEN VIVIAN T; ZHANG YORKE
    权利人:SCRIPPS RESEARCH INST
    摘要:Disclosed herein are compositions, methods, and kits for a cell incorporating unnatural amino acids into an unnatural polypeptide. Also disclosed herein are compositions, methods, and kits for increasing activity and yield of the unnatural polypeptide synthesized by the cell.

    专利号:US-2023037284-A9
    优先权日:2018-11-30
    标题:Combination therapy of peptidomimetic macrocycles
    发明人:GUERLAVAIS VINCENT; ANNIS DAVID ALLEN
    权利人:AILERON THERAPEUTICS INC
    摘要:The present disclosure describes the synthesis of peptidomimetic macrocycles and methods of using peptidomimetic macrocycles to treat a condition. The present disclosure also describes methods of using peptidomimetic macrocycles in combination with at least one additional pharmaceutically-active agent for the treatment of a condition, for example, cancer.

    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.

    专利号:US-2025084410-A1
    优先权日:2015-01-12
    标 题:Incorporation of unnatural nucleotides and methods thereof
    发明人:PTACIN JEROD; MALYSHEV DENIS A; CAFFARO CAROLINA E
    权利人:SYNTHORX INC
    摘要:Disclosed herein are methods, compositions and kits for the synthesis of proteins which comprises unnatural amino acids that utilize a mutant tRNA.
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    参考文献:10.1007/978-94-010-9060-5_230
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