(R)-2-((3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-((4R,6R)-6-(2-hydroxypropan-2-yl)-2,2-dimethyl-1,3-dioxan-4-yl)ethyl acetate | 1428377-55-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-2-((3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-((4R,6R)-6-(2-hydroxypropan-2-yl)-2,2-dimethyl-1,3-dioxan-4-yl)ethyl acetate
• CAS: 1428377-55-2
• 化学式: C₃₅H₅₈O₆
• 分子量: 574.842
• InChiKey: UTRQTFILJWEFDE-VAVMYUGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  41.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  terresterol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 反应 14.0h， 以57%的产率得到(R)-2-((3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-((4R,6R)-6-(2-hydroxypropan-2-yl)-2,2-dimethyl-1,3-dioxan-4-yl)ethyl acetate
  参考文献：
  名称：

  Terresterol, a polyoxygenated lanostanoid, isolated from the oomycete Saprolegnia terrestris, and its innate immune-promoting activity

  摘要：

  Oomycetes are widely spread eukaryotic microorganisms. However, there have only been a few reports on the secondary metabolites produced by them. In the course of screening for innate immune regulators from natural resources, we isolated a new polyoxygenated lanostanoid, terresterol (1), from the oomycetes Saprolegnia terrestris. Compounds bearing a 21,22,24,25-tetraoxygenated side chain similar to 1 have only been rarely described, and the isolation of such compounds shows that oomycetes are promising resources for natural product chemistry. In addition, terresterol (1) has potential to be used as a lead compound for novel immunostimulating agents against bacterial infections and as probe for the innate immune system. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.088