[(3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-17-[(2R)-4-iodobutan-2-yl]-10,13-dimethyl-7-(phenylmethoxymethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate | 1228360-99-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-17-[(2R)-4-iodobutan-2-yl]-10,13-dimethyl-7-(phenylmethoxymethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate
• CAS: 1228360-99-3
• 化学式: C₃₉H₆₃IO₅Si
• 分子量: 766.916
• InChiKey: BKJULQOAQLHBQQ-DQJJCKKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.21
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-17-[(2R)-4-iodobutan-2-yl]-10,13-dimethyl-7-(phenylmethoxymethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate 在 2,4,6-三甲基吡啶 、 二甲基亚砜 作用下， 以80%的产率得到[(3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-17-[(2R)-4-oxobutan-2-yl]-7-(phenylmethoxymethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate
  参考文献：
  名称：

  Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis

  摘要：

  Stereoselective synthesis of the chemoattractant sperm-activating and attracting factor (SAAF), isolated from the eggs of the ascidian Ciona intestinalis, was achieved via reductive 1,3-transposition of an allylic alcohol and the axial opening of an epoxide as key steps. This second-generation synthesis improved the total yield of SAAF over that of the first-generation synthesis and provided a key intermediate for synthesizing molecular probes of SAAF. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.011
• 作为产物：
  描述：

  (4R)-4-[(3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-4-acetyloxy-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-7-(phenylmethoxymethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid 在 碘 、 lead(IV) tetraacetate 作用下， 以 四氯化碳 为溶剂， 以86%的产率得到[(3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-17-[(2R)-4-iodobutan-2-yl]-10,13-dimethyl-7-(phenylmethoxymethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-4-yl] acetate
  参考文献：
  名称：

  Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis

  摘要：

  Stereoselective synthesis of the chemoattractant sperm-activating and attracting factor (SAAF), isolated from the eggs of the ascidian Ciona intestinalis, was achieved via reductive 1,3-transposition of an allylic alcohol and the axial opening of an epoxide as key steps. This second-generation synthesis improved the total yield of SAAF over that of the first-generation synthesis and provided a key intermediate for synthesizing molecular probes of SAAF. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.011