(3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-7-((benzyloxy)methoxy)-3-((tert-butyldimethylsilyl)oxy)-17-((2R,6S,Z)-7-((tert-butyldimethylsilyl)oxy)-6-methylhept-4-en-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-4-ol | 1087282-04-9

• 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)-7-((benzyloxy)methoxy)-3-((tert-butyldimethylsilyl)oxy)-17-((2R,6S,Z)-7-((tert-butyldimethylsilyl)oxy)-6-methylhept-4-en-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-4-ol
• CAS: 1087282-04-9
• 化学式: C₄₇H₈₂O₅Si₂
• 分子量: 783.336
• InChiKey: GNVCJFPRDTVCSP-CEYSAPMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.42
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  苄基氯甲基醚 、 (3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-7-((benzyloxy)methoxy)-3-((tert-butyldimethylsilyl)oxy)-17-((2R,6S,Z)-7-((tert-butyldimethylsilyl)oxy)-6-methylhept-4-en-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-4-ol 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到(((3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-4,7-bis((benzyloxy)methoxy)-17-((2R,6S,Z)-7-((tert-butyldimethylsilyl)oxy)-6-methylhept-4-en-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)(tert-butyl)dimethylsilane
  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：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以98%的产率得到(3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-7-((benzyloxy)methoxy)-3-((tert-butyldimethylsilyl)oxy)-17-((2R,6S,Z)-7-((tert-butyldimethylsilyl)oxy)-6-methylhept-4-en-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-4-ol
  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