(3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one | 215798-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one
• CAS: 215798-01-9
• 化学式: C₁₈H₂₈O₃Si
• 分子量: 320.504
• InChiKey: VQFWUVGLDFHKOA-IMJJTQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到(3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one
  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：

  (2R,3R,4S)-2-Benzyl-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid (S)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl ester 在 palladium dihydroxide 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、405.3 kPa 条件下， 反应 28.0h， 生成 (3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one
  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