4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid | 865704-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid
• 英文别名: (4-((R)-4-benzyl-2-oxooxazolidine-3-yl))-4-oxobutyric acid；(R)-4-(4-benzyl-2-oxooxazolidin-3-yl)-4-oxobutanoic acid
• CAS: 865704-45-6
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: NMNGWXGEAAJMEP-LLVKDONJSA-N

物化性质

• 熔点：
  56 °C(Solvent: Toluene ; Ligroine)
• 沸点：
  517.8±33.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid 在 sodium hexamethyldisilazane 、 phosphorus pentoxide 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 65.0h， 生成 (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-5-(benzyloxy)-5-oxopentanoic acid
  参考文献：
  名称：

  手性琥珀酸盐：对映体纯 β2-氨基酸的前体

  摘要：

  从常见的手性前体叔丁基琥珀酰恶唑烷酮合成了五种适当保护的对映体纯 β(2)-氨基酸，蛋白质 α-氨基酸的同系物。

  DOI：

  10.1055/s-2005-865362
• 作为产物：
  描述：

  丁二酸酐 、 (R)-4-苄基-2-噁唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以96%的产率得到4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid
  参考文献：
  名称：

  手性琥珀酸盐：对映体纯 β2-氨基酸的前体

  摘要：

  从常见的手性前体叔丁基琥珀酰恶唑烷酮合成了五种适当保护的对映体纯 β(2)-氨基酸，蛋白质 α-氨基酸的同系物。

  DOI：

  10.1055/s-2005-865362

文献信息

• Conjugates of Modified Cryptophycins and RGD-Peptides Enter Target Cells by Endocytosis
  作者：Markus Nahrwold、Christine Weiß、Tobias Bogner、Felix Mertink、Jens Conradi、Benedikt Sammet、Ralf Palmisano、Soledad Royo Gracia、Thomas Preuße、Norbert Sewald

  DOI：10.1021/jm301346z

  日期：2013.3.14

  Tumor targeting anticancer drug conjugates that contain a tumor recognition motif (homing device) are of high current relevance. Cryptophycins, naturally occurring cytotoxic cyclo-depsipeptides, have been modified by total synthesis to provide analogues suitable for conjugation to peptide-based homing devices. An array of functionalized beta(2)-amino acids was synthesized and incorporated into cryptophycins. All analogues proved to be highly active in the cytotoxicity assay using the human cervix carcinoma cell line KB-3-1 and its multidrug-resistant subclone KB-V1. Conformational analysis of cryptophycin-52 and two synthetic analogues was performed by NMR and MD methods to obtain information on the influence of the unit C configuration on the overall conformation. An azide-functionalized cryptophycin was connected by CuAAC to an alkyne-containing fluorescently labeled cyclic RGD-peptide as the homing device for internalization studies. Confocal fluorescence microscopy proved integrin-mediated internalization by endocytosis and final lysosomal localization of the cryptophycin prodrug.
• A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents
  作者：Tuan Minh Nguyen、Nguyen Quang Vu、Jean-Jacques Youte、Jacelyn Lau、Angie Cheong、Ying San Ho、Benjamin S.W. Tan、Kanagasundaram Yoganathan、Mark S. Butler、Christina L.L. Chai

  DOI：10.1016/j.tet.2010.09.031

  日期：2010.11

  The synthesis of the chiral core structure of the lissoclimide class of anti-tumour agents containing three rings including a chiral succinimide subunit and an exocyclic double bond has been investigated The compound 7 was obtained without the use of any protecting groups for the alcohol at C-12 via an asymmetric boron-mediated aldol addition as the key step to install the chiral centres of the rare succimmido methanol moiety This was followed by a sequence of lactonisation microwave-assisted amidation and imidation reactions (C) 2010 Elsevier Ltd All rights reserved