(3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate | 60398-41-6

• 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: (3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate
• 英文别名: tert-butyl N-[(1S)-1-benzyl-3-diazo-2-oxopropyl]carbamate；tert-butyl N-[(S)-1-benzyl-3-diazenyl-2-oxopropyl]carbamate；(S)-3-{[(tert-butoxy)carbonyl]amino}-1-diazo-4-phenylbutan-2-one；(N-tert-Butoxycarbonyl-L-phenylalanyl)diazomethane；(S)-1-diazo-3-(N-tert-butoxycarbonyl)amino-4-phenylbutan-2-one；(S)-[3-diazo-2-oxo-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester；(S)-3-(tert-butyloxycarbonylamino)-1-diazo-4-phenylbutan-2-one；(S)-tert-butyl (4-diazo-3-oxo-1-phenylbutan-2-yl)carbamate；tert-butyl (S)-(4-diazo-3-oxo-1-phenylbutan-2-yl)carbamate；tert-butyl (4-diazo-3-oxo-1-phenylbutan-2-yl)carbamate；(S)-3-[[[(1,1-Dimethylethyl)oxy]carbonyl]amino]-2-oxo-1-diazo-4-phenylbutane；1,1-dimethylethyl (S)-[3-diazo-2-oxo-1-(phenylmethyl)propyl]carbamate；tert-butyl N-[(2S,4Z)-4-diazo-3-oxo-1-phenylbutan-2-yl]carbamate
• CAS: 60398-41-6
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: RCMYIGTVOBGQJW-LBPRGKRZSA-N

物化性质

• 熔点：
  63-64 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2927000090

反应信息

• 作为反应物：
  描述：

  (3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate 在 palladium dihydroxide N-甲基吗啉 、 盐酸 、 sodium tetrahydroborate 、 氢气 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 碳酸氢钠 、 1-羟基苯并三唑 、 三乙胺 、 sodium iodide 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 Ac-Ser-Leu-Asn--Ile-Val-OMe
  参考文献：
  名称：

  New hydroxyethylamine HIV protease inhibitors that suppress viral replication

  摘要：

  The synthesis of analogues of AcSerLeuAsn[Phe-HEA-Pro]IleValOMe (1, JG-365; where HEA stands for the hydroxyethylamine unit 2), a tight-binding inhibitor of HIVP, are reported. Systematic modification of the P3 and P3' regions of the inhibitors has led to smaller HIVP inhibitors that inhibit viral replication in HIV-infected and SIV-infected cell cultures. Six aliphatic and/or aromatic derivatives were prepared by replacing residues in the P3 regions of BocLeuAsn[Phe-HEA-Pro]IleValOMe. Aromatic side chains at P3 gave better inhibitors than aliphatic side chains. The better inhibitors in this series contained a beta-naphthylalanine or a biphenyl unit at P3. A second series of HIVP inhibitors were obtained by converting the P3 group into acyl groups. CbzAsn[Phe-HEA-Pro]IlePheOMe and Qua-Asn-[Phe-HEA-Pro]-Ile-Phe-OMe (where Qua = quinolin-2-ylcarbonyl) are potent HIVP inhibitors with K(i) values equal to 1.0 and 0.1 nM, respectively. The inhibition constants were determined by using the continuous fluorometric assay developed by Toth and Marshall. The activities of the protease inhibitors for inhibition of SIV replication were determined in vitro using CEMX174 cells. Inhibition of HIV infection was determined essentially as reported by Pauwels and co-workers. The anti-HIV assay was carried out in culture using CEM cell (a CD4+ lymphocyte line) infected with virus strain HTLV-IIIb with a multiplicity of infection of 0.1. Several analogues inhibited the cytopathic effect at concentrations of 0.1-0.8 mug/mL. These results establish that good inhibitors of HIV protease that inhibit viral replication in infected lymphocytes in in vitro cell assays can be obtained from JG-365 when the AcSerLeu unit is replaced by aromatic acyl derivatives.

  DOI：

  10.1021/jm00099a008
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate
  参考文献：
  名称：

  含有β3-同位氨基酸的TAPP类似物：合成和受体结合。

  摘要：

  含有α，β-杂合肽的β-氨基酸具有拟肽的巨大潜力。在本文中，我们描述了四肽Tyr - d -Ala-Phe-Phe-NH 2（TAPP）的类似物α，β-杂化物的合成及其对μ阿片和δ阿片受体的亲和力。每个氨基酸与置换升或- d -β 3 - ħ α-氨基酸。TAPP类似物的所有α，β杂化物均在溶液中合成，并测试了对μ阿片和δ阿片受体的亲和力。模拟的Tyr-β 3 ħ - d -Ala-PHE-PheNH 2被认为是作为活性与天然四肽。版权所有©2012欧洲肽协会和John Wiley＆Sons，Ltd.

  DOI：

  10.1002/psc.2433

文献信息

• Synthesis of diazoketones derived from α-amino acids; problem of side reactions
  作者：Krystyna Plucińska、Bogdan Liberek

  DOI：10.1016/s0040-4020(01)81643-4

  日期：1987.1

  Optimum conditions of synthesis of eight diazoketones derived from optically active N-(t-butyloxycarbonyl)- and N-benzyloxycarbonylamino acids have been described. The problem of formation of by-products during Arndt-Eistert synthesis of β-homoamino acids at the stage of reaction of mixed anhydride with a weak nucleophile-diazomethane - has been discussed.

  已经描述了合成八种衍生自光学活性的N-（叔丁氧羰基）-和N-苄氧羰基氨基酸的重氮酮的最佳条件。讨论了在混合酸酐与弱亲核试剂-重氮甲烷反应的阶段，在Arndt-Eistert合成β-均氨基酸过程中形成副产物的问题。
• An efficient synthesis of cyclic urethanes from Boc-protected amino acids through a metal triflate-catalyzed intramolecular diazocarbonyl insertion reaction
  作者：Jae-Chul Jung、Mitchell A. Avery

  DOI：10.1016/j.tetlet.2006.08.111

  日期：2006.11

  A simple and efficient synthesis of cyclic urethanes and related oxazinanones 1a–l from diazoketones 3a–l is described. The transformation involves generation of carbenes by activation of diazo groups using metal triflates in intramolecular diazocarbonyl insertion reactions in high overall yields.

  本文描述了由重氮酮3a - 1简单有效地合成环状氨基甲酸酯和相关的恶嗪酮1a - l的方法。该转化涉及在分子内重氮羰基插入反应中使用金属三氟甲磺酸酯通过重氮基团的活化而生成羧甲酸酯，总收率很高。
• Kinetic deconjugation: a gateway to the synthesis of Xxx-Gly (E)-alkene dipeptide isosteres
  作者：Arnaud Proteau-Gagné、Jean-François Nadon、Sylvain Bernard、Brigitte Guérin、Louis Gendron、Yves L. Dory

  DOI：10.1016/j.tetlet.2011.09.136

  日期：2011.12

  A new method for the preparation of Xxx-Gly (E)-alkene dipeptide isosteres (EADIs), using LDA deprotonation followed by 1 N HCl quench, was explored. The method, named kinetic deconjugation, enabled the synthesis of Tyr-Gly, Gly-Gly, Ser-Gly, Pro-Gly, and Phe-Gly EADIs, as well as one Tyr-Gly trisubstituted alkene dipeptide isostere (TADI). Overall, this method, based on commercially available materials

  探索了一种新的制备Xxx-Gly（E）-烯烃二肽等排物（EADIs）的方法，该方法使用LDA脱质子化，然后用1 N HCl淬灭。该方法称为动力学解偶联，能够合成Tyr-Gly，Gly-Gly，Ser-Gly，Pro-Gly和Phe-Gly EADIs，以及一种Tyr-Gly三取代烯烃二肽等排物（TADI）。总体而言，该方法基于可商购的材料，可实现高收率，仅需很少的合成步骤，并且可以在多种EADI的合成中达到克级。
• The Cyclo-β-Tetrapeptide (β-HPhe-β-HThr-β-HLys-β-HTrp): Synthesis, NMR Structure in Methanol Solution, and Affinity for Human Somatostatin Receptors
  作者：Karl Gademann、Martin Ernst、Dieter Seebach、Daniel Hoyer

  DOI：10.1002/(sici)1522-2675(20000119)83:1<16::aid-hlca16>3.0.co;2-3

  日期：2000.1.19

  Z)-OMe. The (N-Me)-β-HThr-(N-Me)-β-HPhe analog was also prepd. C- and N-terminal deprotection and cyclization through the pentafluorophenyl ester gave the insol. beta-tetrapeptide with protected Thr and Lys side chains. Solubilization and debenzylation could only be effected in LiCl-contg. THF (ca. 10% yield; with ca. 55% recovery). HPLC Purifn. provided a sample of the title compd., the structure

  环（β-HAla）4 的已知固态结构用于模拟环-β-四肽（β-HPhe-β-HThr-β-HLys-β-HTrp）的结构，作为一种前瞻性的生长抑素模拟物。合成开始于 N-保护的天然氨基酸 Boc-Phe-OH、Boc-Trp-OH、Boc-Lys(2-Cl-Z)-OH (2-Cl-Z = o-chlorobenzyloxycarbonyl) 和 Boc- Thr(OBn)-OH (Bn = 苄基)，与相应的 β-氨基酸衍生物同源。并与 β-四肽 Boc-β-HTrp-β-HPhe-β-HThr(OBn)-β-HLys(2-Cl-Z)-OMe 偶联。还制备了 (N-Me)-β-HThr-(N-Me)-β-HPhe 类似物。通过五氟苯基酯的C-和N-末端去保护和环化得到insol。具有受保护的 Thr 和 Lys 侧链的 β-四肽。增溶和脱苄基只能在 LiCl-contg 中进行。THF（产率约
• 3,3,3-trifluoro-2-mercaptomethyl-N-tetrazolyl substituted propanamides
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05223516A1

  公开（公告）日：1993-06-29

  Compounds of the formula ##STR1## wherein Y can be tetrazolyl are disclosed. These compounds are useful as cardiovascular agents.

  公开了式子##STR1##中Y可以是四唑基的化合物。这些化合物可用作心血管药物。