(2-methylpropoxy)carbonyl N-[(benzyloxy)carbonyl]-D-valinate | 41445-88-9

• 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: (2-methylpropoxy)carbonyl N-[(benzyloxy)carbonyl]-D-valinate
• 英文别名: 2-methylpropoxycarbonyl (2R)-3-methyl-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 41445-88-9
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: UTDZVSLEGHRUCD-OAHLLOKOSA-N

物化性质

• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2-methylpropoxy)carbonyl N-[(benzyloxy)carbonyl]-D-valinate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 Cbz-D-Val-Ser(TBDMS)(TBDMS)-D-Phe-Ser(TBDMS)(TBDMS)-OH
  参考文献：
  名称：

  Total Synthesis and Assignment of Configuration of Lissoclinamide 7

  摘要：

  The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline --> thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.

  DOI：

  10.1021/ja962859f
• 作为产物：
  描述：

  氯甲酸苄酯 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.83h， 生成 (2-methylpropoxy)carbonyl N-[(benzyloxy)carbonyl]-D-valinate
  参考文献：
  名称：

  HETEROCYCLIC UREA DERIVATIVES AND METHODS OF USE THEREOF

  摘要：

  公式（IA）的化合物及其药用可接受的盐被描述。还描述了它们的制备过程、含有它们的药物组合物、它们作为药物的使用以及它们在治疗细菌感染中的用途。

  公开号：

  US20100317624A1

文献信息

• Pietrzynski, Grzegorz; Kubica, Zbigniew; Rzeszotarska, Barbara, Bulletin of the Polish Academy of Sciences: Chemistry, 1989, vol. 37, # 9-12, p. 363 - 370
  作者：Pietrzynski, Grzegorz、Kubica, Zbigniew、Rzeszotarska, Barbara

  DOI：——

  日期：——
• Preparation and Structure−Activity Relationship of Novel P1/P1‘-Substituted Cyclic Urea-Based Human Immunodeficiency Virus Type-1 Protease Inhibitors
  作者：David A. Nugiel、Kim Jacobs、Tabitha Worley、Mona Patel、Robert F. Kaltenbach、Dayton T. Meyer、Prabhakar K. Jadhav、George V. De Lucca、Thomas E. Smyser、Ronald M. Klabe、Lee T. Bacheler、Marlene M. Rayner、Steven P. Seitz

  DOI：10.1021/jm960083n

  日期：1996.1.1

  A series of novel P1/P1'-substituted cyclic urea-based HIV-1 protease inhibitors was prepared. Three different synthetic schemes were used to assemble these compounds. The first approach uses amino acid-based starting materials and was originally used to prepare DMP 323. The other two approaches use L-tartaric acid or L-mannitol as the starting material. The required four contiguous R,S,S,R centers of the cyclic urea scaffold are introduced using substrate control methodology. Each approach has specific advantages based on the desired P1/P1' substituent. Designing analogs based on the enzyme's natural substrates provided compounds with reduced activity. Attempts at exploiting hydrogen bond sites in the S1/S1' pocket, suggested by molecular modeling studies, were not fruitful. Several analogs had better binding affinity compared to our initial leads. Modulating the compound's physical properties led to a 10-fold improvement in translation resulting in better overall antiviral activity.
• Synthesis and characterization of chiral di(N-protected-α-amino)diazo-β-diketones from α-diazoketones and imidazolides derived from amino acids
  作者：Ibrahim A.M. Saraireh

  DOI：10.1016/j.tetlet.2012.01.093

  日期：2012.4

  Di(N-protected-alpha-amino)diazo-beta-diketones were prepared by the reaction of activated N-protected-alpha-amino acids (imidazolides) with alpha-diazoketones, derived from natural amino acids, in the presence of lithium diisopropylamide in tetrahydrofuran as the solvent at -78 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.
• Lewis acid- and cationic lithium-mediated diastereoselective aldol-type reaction based on a double chiral recognition manner for the asymmetric synthesis of α-substituted serines
  作者：Shigeki Sano、Xiao-Kai Liu、Maki Takebayashi、Yoshimaro Kobayashi、Keiko Tabata、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1016/0040-4039(95)00725-r

  日期：1995.6

  Diastereoselective aldol-type reaction of ethyl (5R or 5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazinecarboxylate (5) with chiral aldehyde 7 was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine, MgBr2-Et(3)N, n-butyllithium, and lithium diisopropylamide. The mediation mode with Sn(II) between (5R or 5S)-5 and 7 proved to be quite different from that with Mg(II). The two aldol products were converted to the corresponding gamma-lactonic alpha-substituted serines (2S)- and (2R)-10.
• [EN] HETEROCYCLIC UREA DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS D'URÉE HÉTÉROCYCLIQUE ET LEURS MÉTHODES D'UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2010142978A1

  公开（公告）日：2010-12-16

  Compounds of formula (IA) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.