CAS: 63039-48-5; (S)-2-((Tert-Butoxycarbonyl)Amino)Pent-4-Ynoic Acid

该化合物是一种化学化合物,其特点是其独特的结构,包括一种丙基基化合物和一个受保护的氨基酸功能."N-BOC"的指定表明,该矿群受一个叔丁基羟基碳基(BOC)组的保护,该组通常用于有机合成,以暂时掩盖氨的活性.该化合物通常用于浸泡合成和药用化学,因为它能够引入碳氢化合物功能,可以参与各种混合反应,包括点击化学.该类的出现允许进一步功能化,使其成为生物活性分子开发中的多功能建筑块.此外,(S)-N-BOC-Progylglycine经常被研究其在药物设计和开发中的潜在应用,特别是针对特定生物路径.(S)的配置表明,其精度对于其生物活动至关重要,因为对应器可以在生物系统中展示截然不同的特性.

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198561-07-8 220497-98-3 63039-46-3

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上下游产品

N-(tert-butyloxycarbonyl) azide L-Propargylglycine tert-butyl dicarbonatedi-tert-butyl dicarbonate (R)-2-aminopent-4-ynoic acid methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate (S)-2-tert-Butoxycarbonylamino-5-(2-fluoro-phenyl)-pent-4-ynoic acid H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid3-(1-benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid (S)-2-((tert-butoxycarbonyl)amino)-4-pentynoic acid benzyl ester

合成工艺路线路线简述

    Tert-Butyl 2,5-Dioxo-4-Prop-2-Ynyl-1,3-Oxazolidine-3-Carboxylate置于o-Propargylquinidine,甲醇,水体系中,用 甲苯,四氢呋喃 作为反应溶剂,化学反应 24.17H,以0.48 Kg的收率获得产物boc-L-炔丙基甘氨酸
    参考文献:氨基甲酸酯保护的α-氨基酸n-羧酸酐的动力学拆分和环状介孔酸酐的不对称化与新型改性金鸡纳生物碱催化剂的手性α-氨基酸和手性半酯的实用合成
    标题:氨基甲酸酯保护的α-氨基酸n-羧酸酐的动力学拆分和环状介孔酸酐的不对称化与新型改性金鸡纳生物碱催化剂的手性α-氨基酸和手性半酯的实用合成
    摘要:描述了氨基甲酸酯保护的α-氨基酸n-羧基酐(unca)的动力学拆分的大规模应用和使用改性金鸡纳生物碱对环状内消旋酸酐的脱对称化.这些不对称反应是在工业规模上合成手性α-氨基酸6和手性半酯2的有效有机催化方法,因为有机催化剂的回收和产物纯化可以通过简单的萃取程序进行,而无需色谱纯化步骤.改性金鸡纳生物碱催化剂(dhqd)2 Aqn和(dhq)2正如邓和同事所报道的,Aqn尚不容易获得,因此不适合工业规模的合成.制备了各种o-烷基化的奎尼丁和奎宁衍生物,并筛选了用醇动力学拆分苯丙氨酸unca的催化剂.发现容易制备的o-炔丙基奎尼丁(opqd)和o-炔丙基奎尼丁(opq)是高度对映选择性和实用的催化剂.这些新的催化剂施加到的手性炔丙基甘氨酸的合成24和bay10-8888 / Pld-118,关键中间体26,在工业规模上,通过unca的动力学拆分22和环状的desymmetrization内消旋-酸酐25.
    DOI:10.1021/op700023H

    海关参考信息

    专利信息


    专利号:US-5665598-A
    优先权日:1994-04-13
    标题:Synthesis of chiral N-protected-α-substituted-glycine free acids by zinc-mediated addition of organic halide to glycine cation equivalent
    发明人:ABOOD NORMAN A; NOSAL ROGER A
    权利人:SEARLE & CO
    摘要:A method is described for synthesis of N-Boc-L-propargylglycine, a key intermediate used in the preparation of high-potency, orally-active renin inhibitors. This method involves reaction of an organic halide with a glycine cation equivalent, such as methyl N-Boc-2-acetoxyglycine, in the presence of zinc dust to give Boc-protected amino acid derivatives in high yield. Typically useful organic halides are allylic, benzylic and propargylic halides. Resolution of methyl N-Boc-propargylglycine with alpha -chymotrypsin provides N-Boc-L-propargylglycine in high yield.

    专利号:US-11708320-B2
    优先权日:2018-06-29
    标 题:Environmentally-friendly hydroazidation of olefins
    发明人:XU HAO
    权利人:UNIV GEORGIA STATE RES FOUND
    摘要:The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.

    专利号:US-11679168-B2
    优先权日:2018-09-14
    标 题 :Caspase-3-triggered molecular self-assembling PET probes and uses thereof
    发明人:RAO JIANGHONG; CHENG YUNFENG; CHEN MIN; XIE JIANGHANG; CHEN ZIXIN
    权利人:UNIV LELAND STANFORD JUNIOR; THE BOARD OF TRUSTEES OF LELAND STANFORD JUNIOR UNIV
    摘要:Embodiments of the synthesis, radiolabeling and biological applications of an activatable tracer that undergoes intramolecular cyclization and aggregation upon activation by cleavage of a blocking moiety are provided. The probes of the disclosure allow for target-controlled self-assembly of small molecules in living subjects for imaging and drug delivery. The aggregated nanoprobes of the disclosure may be detectable optically, by PET detection, magnetic resonance imaging, and the like depending on the detectable reporter attached to the nanoprobe.

    专利号:US-10308595-B2
    优先权日:2013-02-15
    标 题:Albicidin derivatives, their use and synthesis
    发明人:SUESSMUTH RODERICH; KRETZ JULIAN; SCHUBERT VIVIEN; PESIC ALEXANDER; HUEGELLAND MANUELA; ROYER MONIQUE; COCIANCICH STEPHANE; ROTT PHILIPPE; KERWAT DENNIS; GRAETZ STEFAN
    权利人:UNIV BERLIN TECH
    摘要:Antibiotically active compounds characterized by general formula (I), wherein X1, BB, BC, BD, BE and X2 are building blocks with D1, D2, D3, D4 or D5 being linkers which include carbon, sulphur, nitrogen, phosphor and/or oxygen atoms and which are covalently connecting the moities BA and BB, BB and BC, BC and BD, BD and BE and BE and BF, respectively, and wherein in particular the building block BC comprises an amino acid derivative. The compounds for use in a method of treatment of diseases, in particular for use in a method of treatment of bacterial infections are also disclosed.

    专利号:US-5508466-A
    优先权日:1994-04-13
    标题 :Synthesis of N-protected-α-substituted-glycine racemic esters by zinc-mediated addition of organic halide to glycine cation equivalent

    专利号:US-8722014-B2
    优先权日:2009-05-01
    标题 :1 H-[1, 2, 3] triazole substituted amino acids and uses thereof
    发明人:MACH ROBERT H; MCCONATHY JONATHAN
    权利人:MACH ROBERT H; MCCONATHY JONATHAN; UNIV WASHINGTON
    摘要:Tracers for cationic amino acid transport systems and methods of synthesis are disclosed, including compounds comprising a 1H-[1,2,3]triazole moiety. Further disclosed are uses of the analogues, including in vivo imaging of tumors by Positron emission tomography (PET) or Single Photon Emission Computed Tomography (SPECT).
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    主要参考文献

    [参考文献]: Luckose F, Et Al. Effects Of Amino Acid Derivatives On Physical, Mental, And Physiological Activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

    合成参考文献


    摘要:Izawa, K.; Torii, T.; Nishikawa, T.; Imai, H., Science of Synthesis: Asymmetric Organocatalysis, (2012) 2, 848.
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