(2R,3R,4S)-2-benzyl-3-hydroxy-4-benzyloxypentanoic acid | 215798-07-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,3R,4S)-2-benzyl-3-hydroxy-4-benzyloxypentanoic acid
• CAS: 215798-07-5
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: ARPJGXYPKILRGJ-QGTPRVQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2-benzyl-3-hydroxy-4-benzyloxypentanoic acid 在 咪唑 、 4-二甲氨基吡啶 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (2R,3R,4S)-2-Benzyl-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid (S)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl ester
  参考文献：
  名称：

  Total synthesis of the antifungal dilactones UK-2A and UK-3A: The determination of their relative and absolute configurations, analog synthesis and antifungal activities

  摘要：

  The synthesis of the antifungal dilactones, UK-2A and UK-3A, is described. In addition to providing a workable synthetic route to these potent antifungal antibiotics, this has allowed us to determine the assignment of the relative and absolute configurations in the nine-membered ring. Furthermore, UK-2A analogs were also synthesized and evaluated their antifungal activities and cytotoxic activities along with UK-2A, (2R, 3R, 4S, 7R)-UK-2A, UK-3A, (2R, 3R, 4S, 7R)-UK-3A, and antimycin A. The structural requirements for the selective cytotoxicity against yeasts and filamentous fungi will also be suggested. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00777-7
• 作为产物：
  描述：

  (R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 (2R,3R,4S)-2-benzyl-3-hydroxy-4-benzyloxypentanoic acid
  参考文献：
  名称：

  Total synthesis of the antifungal dilactones UK-2A and UK-3A: The determination of their relative and absolute configurations, analog synthesis and antifungal activities

  摘要：

  The synthesis of the antifungal dilactones, UK-2A and UK-3A, is described. In addition to providing a workable synthetic route to these potent antifungal antibiotics, this has allowed us to determine the assignment of the relative and absolute configurations in the nine-membered ring. Furthermore, UK-2A analogs were also synthesized and evaluated their antifungal activities and cytotoxic activities along with UK-2A, (2R, 3R, 4S, 7R)-UK-2A, UK-3A, (2R, 3R, 4S, 7R)-UK-3A, and antimycin A. The structural requirements for the selective cytotoxicity against yeasts and filamentous fungi will also be suggested. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00777-7