(RS)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester | 1016258-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RS)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester
• 英文别名: tert-butyl-3-([(benzyloxy)carbonyl]amino)-4-hydroxybutanoate；1,1-Dimethylethyl 4-hydroxy-3-[[(phenylmethoxy)carbonyl]amino]butanoate；tert-butyl 4-hydroxy-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 1016258-20-0
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: IVQADIBBXAAFHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (RS)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester 在 (COCl₂)2 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 (RS)-4,4-dimethoxy-3-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Enantiomeric Purity of Protectedα-Amino and Peptide Aldehydes

  摘要：

  The synthesis of enantiomerically pure Ac-Tyr-Val-Ala-Asp(O'Bu)-H dimethyl acetal ((S)-1) is reported, a protected tetrapeptide C-terminal aldehyde belonging to a class of potent, reversible inhibitors of cysteine proteases (e.g.. interleukin-1 beta-converting enzyme (ICE), also called caspase-1). The coupling of the precursors Ac-Tyr-Val-Ala-OH ((S)-8) and H-Asp(O'Bu)-H dimethyl acetal ((S)-6) gave (S)-1 in a yield of 85%, with epimerization of < 2% at the alanine and aspartic-acid residue. (S)-6 itself was synthesized in four steps in an overall yield of 83% with an ee >98%.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1960::aid-hlca1960>3.0.co;2-2
• 作为产物：
  描述：

  Cbz-aspartic acid (tert-butyl ester) 在 N-甲基吗啉 、 sodium tetrahydroborate 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 (RS)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Enantiomeric Purity of Protectedα-Amino and Peptide Aldehydes

  摘要：

  The synthesis of enantiomerically pure Ac-Tyr-Val-Ala-Asp(O'Bu)-H dimethyl acetal ((S)-1) is reported, a protected tetrapeptide C-terminal aldehyde belonging to a class of potent, reversible inhibitors of cysteine proteases (e.g.. interleukin-1 beta-converting enzyme (ICE), also called caspase-1). The coupling of the precursors Ac-Tyr-Val-Ala-OH ((S)-8) and H-Asp(O'Bu)-H dimethyl acetal ((S)-6) gave (S)-1 in a yield of 85%, with epimerization of < 2% at the alanine and aspartic-acid residue. (S)-6 itself was synthesized in four steps in an overall yield of 83% with an ee >98%.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1960::aid-hlca1960>3.0.co;2-2

文献信息

• Beta-alanine derivative and a process for the preparation thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：US20010051730A1

  公开（公告）日：2001-12-13

  This invention relates to &bgr;-alanine derivatives represented by the following formula: 1 wherein each symbol is as defined in the specification and pharmaceutically acceptable salt thereof which is glycoprotein IIb/IIIa antagonist, inhibitor of blood platelets aggregation and inhibitor of the binding of fibrinogen to blood platelets, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method for the prevention and/or treatment diseases indicated in the specification to a human being or an animal.

  本发明涉及以下公式所表示的&bgr;-丙氨酸衍生物：1其中每个符号如说明书所定义的，并且其药学上可接受的盐是糖蛋白IIb/IIIa拮抗剂，血小板聚集抑制剂和纤维蛋白原与血小板结合的抑制剂，涉及其制备方法，包括它的制药组合物，以及用于预防和/或治疗说明书中所指示的人类或动物疾病的方法。
• N-(3-piperidinylcarbonyl)-beta-alanine derivatives as paf antagonists
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1106606A2

  公开（公告）日：2001-06-13

  This invention relates to β-alanine derivatives represented by the following formula : wherein each symbol is as defined in the specification and pharmaceutically acceptable salt thereof which is glycoprotein IIb/IIIa antagonist, inhibitor of blood platelets aggregation and inhibitor of the binding of fibrinogen to blood platelets, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method for the prevention and/or treatment diseases indicated in the specification to a human being or an animal.

  本发明涉及由下式表示的 β-丙氨酸衍生物： 其中各符号如说明书中所定义，以及其药学上可接受的盐，它们是糖蛋白 IIb/IIIa 拮抗剂、血小板聚集抑制剂和纤维蛋白原与血小板结合抑制剂，还涉及其制备工艺、包含这些衍生物的药物组合物以及对人类或动物预防和/或治疗说明书中所述疾病的方法。
• (ANTI-HER2 ANTIBODY)-DRUG CONJUGATE
  申请人：Daiichi Sankyo Co., Ltd.

  公开号：EP3130608A1

  公开（公告）日：2017-02-15

  As an antitumor drug which is excellent in terms of antitumor effect and safety and has an excellent therapeutic effect, there is provided an antibody-drug conjugate in which an antitumor compound represented by the following formula is conjugated to an anti-HER2 antibody via a linker having a structure represented by the formula: L1-L2-LP-NH-(CH2)n1-La-Lb-Lc or -L1-L2-LP-wherein the anti-HER2 antibody is connected to the terminal L1, and the antitumor compound is connected to the terminal Lc or LP with the nitrogen atom of the amino group at position 1 as the connecting position.

  作为一种抗肿瘤效果和安全性极佳且治疗效果极佳的抗肿瘤药物，本发明提供了一种抗体-药物共轭物，其中下式表示的抗肿瘤化合物通过具有下式表示的结构的连接体与抗 HER2 抗体共轭：L1-L2-LP-NH-(CH2)n1-La-Lb-Lc或-L1-L2-LP-其中，抗 HER2 抗体与末端 L1 连接，抗肿瘤化合物与末端 Lc 或 LP 连接，连接位置为 1 位氨基的氮原子。
• (Anti-HER2 antibody)-drug conjugate
  申请人：DAIICHI SANKYO COMPANY, LIMITED

  公开号：US11185594B2

  公开（公告）日：2021-11-30

  As an antitumor drug which is excellent in terms of antitumor effect and safety and has an excellent therapeutic effect, there is provided an antibody-drug conjugate in which an antitumor compound represented by the following formula is conjugated to an anti-HER2 antibody via a linker having a structure represented by the formula: L1-L2-LP-NH—(CH2)n1-La-Lb-Lc or -L1-L2-LP- wherein the anti-HER2 antibody is connected to the terminal L1, and the antitumor compound is connected to the terminal Lc or LP with the nitrogen atom of the amino group at position 1 as the connecting position.

  作为一种抗肿瘤效果和安全性极佳且治疗效果极佳的抗肿瘤药物，本发明提供了一种抗体-药物共轭物，其中下式所代表的抗肿瘤化合物通过具有式所代表结构的连接体与抗 HER2 抗体共轭：L1-L2-LP-NH-(CH2)n1-La-Lb-Lc或-L1-L2-LP-，其中抗 HER2 抗体与末端 L1 连接，抗肿瘤化合物与末端 Lc 或 LP 连接，以位于第 1 位的氨基的氮原子为连接位。
• N-(3-PIPERIDINYLCARBONYL)-BETA-ALANINE DERIVATIVES AS PAF ANTAGONISTS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0669912B1

  公开（公告）日：2001-12-05