(4R,5S,2'R,3'S)-3-(3'-hydroxy-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone | 260395-13-9

• 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: (4R,5S,2'R,3'S)-3-(3'-hydroxy-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone
• 英文别名: (4R,5S)-[(2R,3S)-3-hydroxy-2-methylhexanoyl]-4-methyl-5-phenyl-2-oxazolidinone；(4R,5S)-3-[(2R,3S)-3-hydroxy-2-methylhexanoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 260395-13-9
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: LKBHRFKNNYTDIS-RJZRQDKASA-N

物化性质

• 沸点：
  480.3±45.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S,2'R,3'S)-3-(3'-hydroxy-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone 在 吡啶 、 锂硼氢 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2S,3S)-2-methyl-1-tosyloxy-3-hexanol
  参考文献：
  名称：

  Asymmetric synthesis of phoenicol, ferrugineol and cruentol, aggregation pheromones of Rhynchophorus spp.

  摘要：

  Syntheses of phoenicol, ferrugineol, and cruentol, aggregation pheromones of Rhynchophorus palm weevils, have been achieved with an overall yield of 42, 40 and 41%, respectively (five steps), in high enantiomeric purity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00528-5
• 作为产物：
  描述：

  (4R,5S)-(+)-4-甲基-5-苯基-2-恶唑啉酮 在 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4R,5S,2'R,3'S)-3-(3'-hydroxy-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone
  参考文献：
  名称：

  ulongamide A的全合成，一种从海洋蓝细菌Lyngbya sp。分离的环状二肽。

  摘要：

  ulongamide A（1）是一种具有细胞毒性的天然环状二肽肽，是通过一条收敛性路线实现的，该路线涉及将片段7和8与五肽24偶联，然后在先去除t- Boc保护基团之后将其环化。

  DOI：

  10.1016/j.tetlet.2006.11.117

文献信息

• Synthesis of <i>O</i>-Me Ulongamide B and <i>O</i>-Me Ulongamide C, Natural Modified Cyclodepsipeptides
  作者：Cuauhtémoc Alvarado、Gerardo Hernández、Eduardo Díaz、José D. Soano、Miguel A. Vilchis-Reyes、Miguel A. Martínez-Urbina、Angel Guzmán

  DOI：10.1080/00397911.2011.618284

  日期：2013.3.1

  Synthesis of O-Me ulongamide B and O-Me ulongamide C, modified natural cyclodepsipeptides, was achieved by a convergent route. The respective dipeptides and tridepsipeptides were coupled, obtaining linear depsipentapeptides, which were then deprotected and cyclized. These compounds were tested against three different types of human carcinoma cells and showed only moderate activity.
• Kulokekahilide-1, a Cytotoxic Depsipeptide from the Cephalaspidean Mollusk <i>Philinopsis speciosa</i>
  作者：Junji Kimura、Yuuki Takada、Tomoko Inayoshi、Yoichi Nakao、Gilles Goetz、Wesley Y. Yoshida、Paul J. Scheuer

  DOI：10.1021/jo010176z

  日期：2002.3.1

  The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 mug/mL.
• Total synthesis of ulongamide A, a cyclic depsipeptide isolated from marine cyanobacteria Lyngbya sp.
  作者：Cuauhtémoc Alvarado、Eduardo Díaz、Ángel Guzmán

  DOI：10.1016/j.tetlet.2006.11.117

  日期：2007.1

  A total synthesis of ulongamide A (1), a cytotoxic natural cyclic depsipeptide, was achieved by a convergent route involving coupling of the fragments 7 and 8 to the pentapeptide 24, and subsequent cyclization thereof after prior removal of the t-Boc protecting groups.

  ulongamide A（1）是一种具有细胞毒性的天然环状二肽肽，是通过一条收敛性路线实现的，该路线涉及将片段7和8与五肽24偶联，然后在先去除t- Boc保护基团之后将其环化。
• Asymmetric synthesis of phoenicol, ferrugineol and cruentol, aggregation pheromones of Rhynchophorus spp.
  作者：José M Odriozola、Jesús M Garcı́a、Alberto González、Pilar Gil

  DOI：10.1016/s0957-4166(99)00528-5

  日期：1999.12

  Syntheses of phoenicol, ferrugineol, and cruentol, aggregation pheromones of Rhynchophorus palm weevils, have been achieved with an overall yield of 42, 40 and 41%, respectively (five steps), in high enantiomeric purity. (C) 1999 Elsevier Science Ltd. All rights reserved.