methyl (4R)-4-[(7R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-7-(phenylmethoxymethoxy)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate | 1228360-88-0

• 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: methyl (4R)-4-[(7R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-7-(phenylmethoxymethoxy)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1228360-88-0
• 化学式: C₃₃H₄₆O₅
• 分子量: 522.725
• InChiKey: ILOPXVCEZCFILA-VWWIIVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-[(7R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-7-(phenylmethoxymethoxy)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到methyl (4R)-4-[(3S,7R,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7-(phenylmethoxymethoxy)-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  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：

  methyl 3-oxo-7α-benzyloxymethyl-5β-cholan-24-oate 在 三氟乙酸 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 以68%的产率得到methyl (4R)-4-[(7R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-7-(phenylmethoxymethoxy)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
  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

文献信息

• Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis
  作者：Tohru Oishi、Kouichiro Ootou、Hajime Shibata、Michio Murata

  DOI：10.1016/j.tetlet.2010.03.011

  日期：2010.5

  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.