phenylmethyl (4S)-4-(t-butyloxycarbonyl)amino-3-oxopentanoate | 187806-88-8

• 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: phenylmethyl (4S)-4-(t-butyloxycarbonyl)amino-3-oxopentanoate
• 英文别名: (4S)-N-Boc-4-amino-3-oxo-pentanoic acid benzyl ester；(4S)-benzyl N-Boc-4-amino-3-oxopentanoate；benzyl (4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopentanoate
• CAS: 187806-88-8
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: MWLJEVZLDODWIW-LBPRGKRZSA-N

物化性质

• 沸点：
  440.3±30.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenylmethyl (4S)-4-(t-butyloxycarbonyl)amino-3-oxopentanoate 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， -5.0~25.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (S)-2-((S)-4-tert-Butoxycarbonylamino-3-oxo-pentanoylamino)-propionic acid benzyl ester
  参考文献：
  名称：

  多拉司他丁。26. Dolastatin 111a 的合成和立体化学

  摘要：

  海兔 Dolabella auricularia 的强效抗肿瘤剂 dolastatin 11 的首次合成证实了该天然产物和 dolastatin 12、majusculamide C 和 57-normajusculamide C 的拟议结构并建立了最后构型。

  DOI：

  10.1021/ja963857y
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 乙酸苄酯 在 N,N'-羰基二咪唑 、 lithium diisopropyl amide 作用下， 生成 phenylmethyl (4S)-4-(t-butyloxycarbonyl)amino-3-oxopentanoate
  参考文献：
  名称：

  多拉司他丁。26. Dolastatin 111a 的合成和立体化学

  摘要：

  海兔 Dolabella auricularia 的强效抗肿瘤剂 dolastatin 11 的首次合成证实了该天然产物和 dolastatin 12、majusculamide C 和 57-normajusculamide C 的拟议结构并建立了最后构型。

  DOI：

  10.1021/ja963857y

文献信息

• Peptide deformylase inhibitors with non-peptide scaffold: Synthesis and structure–activity relationships
  作者：Seung Kyu Lee、Kwang Hyun Choi、Sang Jae Lee、Jong Sun Lee、Ji Yun Park、B. Moon Kim、Bong Jin Lee

  DOI：10.1016/j.bmcl.2010.11.056

  日期：2011.1

  Peptide deformylase (PDF), which removes the formyl group at the N-terminal methionine residue of nascent protein, has been recognized as a potent target for antibacterial therapy. We report herein the synthesis and structure-activity relationship studies of non-peptide PDF inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.
• Chain extension of amino acid skeletons: preparation of ketomethylene isosteres
  作者：Cory R Theberge、Charles K Zercher

  DOI：10.1016/s0040-4020(03)00052-8

  日期：2003.2

  Ketomethylene isosteric replacements for peptide bonds were generated through a zinc carbenoid-mediated chain extension reaction in which a variety of amino acid-derived beta-keto esters are converted to gamma-keto esters in a single step. The reaction tolerates a variety of protecting groups and amino acid side chains with no epimerization of the amino acid stereocenter. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Cyclic Depsipeptides, Grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea <i>Leptolyngbya</i> Cyanobacterium
  作者：Christopher C. Thornburg、Muralidhara Thimmaiah、Lamiaa A. Shaala、Andrew M. Hau、Jay M. Malmo、Jane E. Ishmael、Diaa T. A. Youssef、Kerry L. McPhail

  DOI：10.1021/np200270d

  日期：2011.8.26

  Two new grassypeptolides and a lyngbyastatin analogue, together with the known dolastatin 12, have been isolated from field collections and laboratory cultures of the marine cyanobacterium Leptolyngbya sp. collected from the SS Thistlegorm shipwreck in the Red Sea. The overall stereostructures of grassypeptolides D (1) and E (2) and Ibu-epidemethoxylyngbyastatin 3 (3) were determined by a combination of 1D and 2D NMR experiments, MS analysis, Marfey's methodology, and HPLC-MS. Compounds 1 and 2 contain 2-methyl-3-aminobutyric acid and 2-aminobutyric acid, while biosynthetically distinct 3 contains 3-amino-2-methylhexanoic acid and the beta-keto amino acid 4-amino-2,2-dimethyl-3-oxopentanoic acid (Ibu). Grassypeptolides D (1) and E (2) showed significant cytotoxicity to HeLa (IC50 = 335 and 192 nM, respectively) and mouse neuro-2a blastoma cells (IC50 = 599 and 407 nM, respectively), in contrast to Ibu-epidemethoxylyngbyastatin 3 (neuro-2a cells, IC50 > 10 mu M) and dolastatin 12 (neuro-2a cells, IC50 > 1 mu M).
• Isolation and Structure Determination of Lyngbyastatin 3, a Lyngbyastatin 1 Homologue from the Marine Cyanobacterium <i>Lyngbya </i><i>m</i><i>ajuscula.</i> Determination of the Configuration of the 4-Amino-2,2-dimethyl-3-oxopentanoic Acid Unit in Majusculamide C, Dolastatin 12, Lyngbyastatin 1, and Lyngbyastatin 3 from Cyanobacteria
  作者：Philip G. Williams、Richard E. Moore、Valerie J. Paul

  DOI：10.1021/np0302145

  日期：2003.10.1

  The structure of lyngbyastatin 3 (1), including the configurations of the two unusual amino acid residues, viz., the 3-amino-2-methylhexanoic acid (Amha) and 4-amino-2,2-dimethyl-3-oxopentanoic acid units (Ibu), has been established by chemical degradation. Analysis of the cyanobacterial samples of lyngbyastatin 3 (1), lyngbyastatin 1 (2), and dolastatin 12 (3) demonstrated that they are mixtures of Ibu epimers [R (major) and S (minor)], whereas the structurally related majusculamide C (4) is a single diastereomer having an S-Ibu unit.
• Dolastatins. 26. Synthesis and Stereochemistry of Dolastatin 11¹^a
  作者：Robert B. Bates、Kennard G. Brusoe、Jennifer J. Burns、Sriyani Caldera、Wei Cui、Sanjeev Gangwar、Michelle R. Gramme、Kelly J. McClure、Gregory P. Rouen、Heiko Schadow、Chad C. Stessman、Stuart R. Taylor、Vicky H. Vu、Gayle V. Yarick、Jianxing Zhang、George R. Pettit、Roger Bontems

  DOI：10.1021/ja963857y

  日期：1997.3.1

  The first synthesis of dolastatin 11, a potent antineoplastic agent from the sea hare Dolabella auricularia, confirmed the proposed structure and established the last configuration in this natural product and in dolastatin 12, majusculamide C, and 57-normajusculamide C.

  海兔 Dolabella auricularia 的强效抗肿瘤剂 dolastatin 11 的首次合成证实了该天然产物和 dolastatin 12、majusculamide C 和 57-normajusculamide C 的拟议结构并建立了最后构型。