CAS: 122672-46-2; Cispentacin

该化合物是一种手性非蛋白性氨基酸,其基质为环戊烷脊椎,分别位于1和2个位置上,有氨基和碳苯基功能组,其硬性环状结构和立体化学使其在不对称合成,浸泡物改造和药物研究中具有价值.该化合物是设计小儿科和受限制类的多功能构件,可加强代谢稳定性和生物活性分子的相容性控制.其高度的耐受性及其与固相容性丙酸合成的兼容性进一步支持其在药用化学和药物开发中的效用.该产品通常配有严格的质量控制,以确保研究应用的一致性.

结构式图片

相似化合物

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合成工艺路线路线简述

    (1R.2S)-2-(Boc-氨基)环戊烷甲酸置于盐酸体系中,化学反应 1.0H,以80%的收率获得(1R,2S)-2-氨基-1-环戊烷羧酸
    参考文献:Synthesis Of Racemic And Optically Active Cispentacin (Fr109615) Using Intramolecular Nitrone-Olefin Cycloaddition.
    标题:Synthesis Of Racemic And Optically Active Cispentacin (Fr109615) Using Intramolecular Nitrone-Olefin Cycloaddition.
    摘要:本文介绍了外消旋且具有光学活性的西苯达辛((-)-1)的合成.烯基腈酮 7 分子内的硝酮-烯烃环加成反应产生了顺式异恶唑烷 (+/-)-8,通过催化氢解和氧化的连续反应,将其转化为 (+/-)-1.同样,光学活性腈酮 (R)-22 也是通过脂肪酶催化水解醋酸酯 (+/-)-17 从酮 15 中得到的,经过分子内环加成反应,以高立体选择性(15:1)得到 (+)-25.环加成产物 (+)-25 经过 4 个步骤转化为具有光学活性的天然西司喷丁.
    Doi:10.1248/cpb.41.1012

    海关参考信息

    专利信息


    专利号:US-9353057-B2
    优先权日:2003-12-30
    标 题:Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
    发明人:GALLOP MARK A; DAI XUEDONG; SCHEUERMAN RANDALL A; RAILLARD STEPHEN P; MANTHATI SURESH K; YAO FENMEI; PHAN THU; LUDWIKOW MARIA; PENG GE; BHAT SEEMA
    权利人:XENOPORT INC
    摘要:Methods for synthesis of 1-(acyloxy)-alkyl carbamates, particularly, the synthesis of 1-(acyloxy)-alkyl carbamate prodrugs of primary or secondary amine-containing drugs are described. Also described are methods for synthesis of 1-(acyloxy)-alkyl N-hydroxysuccinimidyl carbonates which are useful intermediates in the synthesis of 1-(acyloxy)-alkyl carbamates are also described.

    专利号:US-9206222-B2
    优先权日:2009-06-29
    标题:Solid phase peptide synthesis of peptide alcohols
    发明人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN
    权利人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN; CENTRE NAT RECH SCIENT
    摘要:The present invention relates to the synthesis of depsipeptides on solid phase support. Said depsipeptides are then implicated in a solution phase O—N acyl shift enabling to obtain the corresponding peptide alcohols.

    专利号:US-2015158809-A9
    优先权日:2013-02-26
    标 题 :Method of making 1-(acyloxy)-alkyl carbamate compounds
    发明人:WANG HUAN; LIU PENG; DAI QUNYING; YIN HAO; RAILLARD STEPHEN P
    权利人:XENOPORT INC
    摘要:Methods of preparing carbamate prodrugs of amine-containing drugs are provided. Carbonates useful in the synthesis of the carbamate prodrugs are also provided.

    专利号:US-2023295613-A1
    优先权日:2020-02-14
    标 题:Long chain carbon and cyclic amino acids substrates for genetic code reprogramming
    发明人:JEWETT MICHAEL C; LEE JOONGOO; MOORE JEFFREY S; SCHWARZ KEVIN J
    权利人:UNIV NORTHWESTERN; UNIV ILLINOIS
    摘要:Abstract: Disclosed are methods, systems, components, and compositions for synthesis of sequence defined polymers. The methods, systems, components, and compositions may be utilized for incorporating novel substrates that include non-standard amino acid monomers and non-amino acid monomers into sequence defined polymers. As disclosed herein, the novel substrates may be utilized for acylation of tRNA via flexizyme catalyzed reactions. The tRNAs thus acylated with the novel substrates may be utilized in synthesis platforms for incorporating the novel substrates into a sequence defined polymer.

    专利号:WO-2011000848-A1
    优先权日:2009-06-29
    标题 :Solid phase peptide synthesis of peptide alcohols

    专利号:WO-9218477-A1
    优先权日:1991-04-19
    标题 :Azabicycloheptanone
    发明人:EVANS CHRISTOPHER THOMAS; ROBERTS STANLEY MICHAEL; SUTHERLAND ALAN GORDON
    权利人:CHIROS LTD
    摘要:The individual enantiomers of the bicyclic β-lactam compounds (Ia), (Ib), (IIa) or (IIb), optionally substituted by non-interfering substituent(s). The novel enantiomers can be obtained by biotransformation. The Ia or IIa compounds can be used for the synthesis of chiral cis-pentacin.
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    合成参考文献


    摘要:Journal of Antibiotics., 42(1756), 1989 []
    参考文献:10.1002/chem.201203183
    摘要:Kiss L, Cherepanova M, Forró E, Fülöp F. A new access route to functionalized cispentacins from norbornene β-amino acids. Chemistry. 2013 Feb 04;19(6):2102–7. doi: 10.1002/chem.201203183.
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