(S)-N-tert-butyloxycarbonylaspartic acid dibenzyl ester | 80974-42-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-tert-butyloxycarbonylaspartic acid dibenzyl ester
• 英文别名: N-tert-butyloxycarbonyl-L-aspartic acid dibenzyl ester；Boc-Asp(OBzl)OBzl；N-t-BOC-L-Aspartic acid dibenzyl ester；Boc-Asp(Obzl)-Obzl；dibenzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate
• CAS: 80974-42-1
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: ORYQVZVMWMCZSK-IBGZPJMESA-N

物化性质

• 沸点：
  548.9±50.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-tert-butyloxycarbonylaspartic acid dibenzyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 L-天冬氨酸二苄酯
  参考文献：
  名称：

  通过改变萘二酰亚胺中的取代基可调谐聚集诱导有机纳米粒子的多色发射

  摘要：

  在本文中，我们设计了升天冬氨酸联萘二酰亚胺（NDI）为基础的具有苄基酯基团在两个具有不同取代基的端子（NAB-两性分子1 - 5）。明智地将取代基从诸如硝基苯的吸电子基团（EWG）修饰为给电子基团（EDG），甲氧基苯，最后修饰为扩展的芳族残基（萘）以调节NDI末端的π电子密度衍生品。所有合成的NDI衍生物都分子溶解在二甲基亚砜（DMSO）中，并且随着DMSO溶液中水含量的增加，NDI衍生物开始通过J自组装。-含水量在40％或以上时的聚集体。通过显微镜研究对在99％水中的DMSO（f w = 99％）中形成的自组装球形有机纳米颗粒进行了表征。所有的NDI衍生物在分子溶解状态（DMSO）中均显示出非常弱的发射。通过准分子形成，在自组装状态下观察到NDI衍生物（NAB- 1除外）的聚集诱导发射（AIE）。在350 nm处激发后，这些基于NDI的AIE发光剂（AIE-gens）（NAB- 2 –

  DOI：

  10.1021/acs.langmuir.8b02996
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 (S)-N-tert-butyloxycarbonylaspartic acid dibenzyl ester
  参考文献：
  名称：

  Chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane, precursor for carbocyclic nucleoside synthesis. Dieckmann cyclization with an .alpha.-amino acid

  摘要：

  Carbocyclic nucleosides are important isosteres of nucleosides possessing a variety of antiviral and antineoplastic activities. We report here a new method for the chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane. This compound is a key precursor for the synthesis of some carbocyclic nucleosides. The method involves (1) an improved synthesis of (S)-2-aminoadipic acid; (2) Dieckmann cyclization of this alpha-amino acid to an aminocyclopentanone; and (3) elaboration of the latter to the target (1S,3R)-l-amino-3-(hydroxymethyl)cyclopentane. The starting (S)-2-aminoadipic acid delta-methyl ester was prepared enantiomerically pure from (S)-aspartic acid in 51% overall yield. Dieckmann condensation converted this amino acid to a (methoxycarbonyl)-cyclopentanone, and reduction of the ketone followed by elimination yielded (S)-3-[N-(9-phenylfluoren-9-yl)amino]-1-(methoxycarbonyl)cyclopentene. Reduction of the double bond gave a mixture of the cis and trans diastereomers. This mixture was converted to a single diastereomer by epimerization and trapping of the cis isomer as (1S,4R)-2-(9-phenylfluoren-9-yl)-2-azabicyclo[2.2.1]heptan-3-one. Hydrolytic cleavage of the lactam followed by reduction gave (IS,3R)-1-amino-3-(hydroxymethyl)-cyclopentane.

  DOI：

  10.1021/jo00061a006

文献信息

• Mechanistic Insight into the Inactivation of Carboxypeptidase A by α-Benzyl-2-oxo-1,3-oxazolidine-4-acetic Acid, a Novel Type of Irreversible Inhibitor for Carboxypeptidase A with No Stereospecificity
  作者：Sang J. Chung、Suhman Chung、Hyun Soo Lee、Eun-Jung Kim、Kyung Seok Oh、Hyuk Soon Choi、Kwang S. Kim、Yeoun Jin Kim、Jong Hoon Hahn、Dong H. Kim

  DOI：10.1021/jo010421e

  日期：2001.9.1

  stereospecificity shown in the inactivation led us to propose that the ring cleavage occurs by the nucleophilic attack at the 2-position rather than at the 5-position and the ring opening takes place in an addition-elimination mechanism. The tetrahedral transition state that would be generated in this pathway is thought to be stabilized by the active site zinc ion, which was supported by the PM3 semiemprical calculations

  根据羧肽酶A（CPA）的活性位点拓扑结构和酶催化机制，原型为含锌的蛋白水解酶，α-苄基-2-氧代-1,3-恶唑烷-4-乙酸（1）为被设计为一种新型的基于机制的酶灭活剂。从光学活性的天冬氨酸开始，以对映体纯的形式合成了抑制剂的所有四种可能的立体异构体，并对它们的CPA抑制活性进行了评估，发现令人惊讶的是，所有四种立体异构体均以时间依赖性方式抑制了CPA。透析后，抑制的酶没有恢复其酶活性。灭活被2-苄基琥珀酸阻止，后者是一种竞争性抑制剂，已知能与酶的活性位点结合。这些动力学结果强烈支持灭活剂在活性位点共价附于酶。对失活的CPA的ESI质谱数据进行分析，从动力学结果可以得出结论。二阶抑制率常数（k（obs）/ [I]（o））的值在1.7-3.6 M（-1）min（-1）的范围内。失活中缺乏立体定向性，导致我们提出环裂解是通过亲核攻击在2位而不是5位发生的，开环发生在加成消除机理中。认为该途径将产
• CYSTEINE PROTEASE INHIBITORS
  申请人：Unoki Gen

  公开号：US20090291945A1

  公开（公告）日：2009-11-26

  To provide a compound having an excellent cysteine protease inhibitory effect, and to provide a drug for treatment or prevention of the disease selected from the group consisting of osteoporosis, osteoarthritis, chronic rheumatoid arthritis, Paget's disease of bone, hypercalcemia, bone metastasis of cancer, and ostealgia. A compound represented by formula (1) or a pharmaceutically acceptable salt thereof, or a drug or pharmaceutical composition containing the same as an effective component.

  提供一种具有优异半胱氨酸蛋白酶抑制作用的化合物，并提供一种用于治疗或预防骨质疏松症、骨关节炎、慢性类风湿性关节炎、骨Paget病、高钙血症、骨癌转移和骨痛的药物。化合物由式（1）表示，或其药学上可接受的盐，或将其作为有效成分的药物或药物组合物。
• Designer peptide dendrimers using click reaction
  作者：V. Haridas、Yogesh K. Sharma、Srikanta Sahu、Ram P. Verma、Sandhya Sadanandan、Bharat G. Kacheshwar

  DOI：10.1016/j.tet.2011.01.023

  日期：2011.3

  We designed and synthesized various peptide dendrimers using a 1,3-dipolar cycloaddition (Click) reaction. The dendritic structures reported here include symmetrical, asymmetrical, and cationic dendrimers with triazole, cystine, aromatic, aliphatic, and Lys-Asp dipeptide cores. The high chemoselectivity of the click reaction allowed us to synthesize good yields of high-purity protected and unprotected dendritic structures. Triazole is an excellent peptide bond mimic, which remains hydrolytically stable. Dendrimer 15a and the core unit 21 gelate in a mixture of organic solvents. We also demonstrated the versatility of the design by synthesizing various carbohydrate-based dendrimers. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of Optically Active 2-Alkyl-3,4-iminobutanoic Acids. β-Amino Acids Containing an Aziridine Heterocycle
  作者：Jeong-il Park、Guan Rong Tian、Dong H. Kim

  DOI：10.1021/jo0014055

  日期：2001.6.1

  All four stereoisomers of 2-alkyl-3,4-iminobutanoic acid, a novel class of beta -amino acids bearing a chemically versatile aziridine ring, were synthesized starting with aspartic acid. The synthetic strategy involves the introduction of an alkyl group at the beta -position of fully protected optically active aspartic acid followed by the construction of an aziridine ring making use of the alpha -carboxylate and alpha -amino groups. The alpha -carboxylate was reduced to the corresponding alcohol, which was then subjected to cyclization to form an aziridine ring with the N-protected amino group. Removal of the protection groups yielded the target compounds.
• Irreversible inhibition of zinc-containing protease by oxazolidinone derivatives. Novel inactivation chemistry
  作者：Dong H. Kim、Sang Jeon Chung、Eun-Jung Kim、Guan Rong Tian

  DOI：10.1016/s0960-894x(98)00123-1

  日期：1998.4

  alpha-Benzyl-2-oxo-1,3-oxazolidine-4-acetic acid (BOOA) having (alpha R,4S) and (alpha S,4R) configurations were designed and synthesized as a novel type of mechanism-based inactivators for carboxypeptidase A (CPA), and kinetic analysis demonstrated that they indeed inhibit the enzyme in a time-dependent manner with the second order inhibitory rate constants (k(inact)/K-I) of 1.52 and 1.39 M-1 s(-1) for (alpha S,4R)-BOOA and (alpha R,4S)-BOOA, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.