22(R)-hydroxy-3α,5-cyclo-6β-methoxy-5α-cholane-23(E)-ene | 70813-70-6

• 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: 22(R)-hydroxy-3α,5-cyclo-6β-methoxy-5α-cholane-23(E)-ene
• 英文别名: (22S,23E)-6β-methoxy-3α,5-cyclo-5α-cholest-23-en-22-ol；(E,2S,3S)-2-[(1S,2R,5R,7R,8R,10S,11S,14R,15S)-8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]-6-methylhept-4-en-3-ol
• CAS: 70813-70-6
• 化学式: C₂₈H₄₆O₂
• 分子量: 414.672
• InChiKey: XFFVCQNJVTVBLH-KFEUCHPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  22(R)-hydroxy-3α,5-cyclo-6β-methoxy-5α-cholane-23(E)-ene 在 吡啶 作用下， 生成 (22S)-cholest-5-ene-3β,22-diol 3,22-diacetate
  参考文献：
  名称：

  Stereospecific synthesis of the side chain of the steroidal plant sex hormone oogoniol

  摘要：

  DOI：

  10.1021/jo01333a021
• 作为产物：
  描述：

  (E)-1-(3-methyl1-butenyl)boronic acid 在 sodium hydroxide 、 碘 作用下， 以 乙醚 为溶剂， 生成 22(R)-hydroxy-3α,5-cyclo-6β-methoxy-5α-cholane-23(E)-ene
  参考文献：
  名称：

  Stereospecific synthesis of the side chain of the steroidal plant sex hormone oogoniol

  摘要：

  DOI：

  10.1021/jo01333a021

文献信息

• C-24 Stereochemistry of Marine Sterols: (22E)-24-(Isopropenyl)-22-dehydrocholesterol and 24-Isopropenylcholesterol
  作者：Shizue Echigo、Noriyuki Hara、Gladys Jeanette Carderon、Carmenza Duque、Yoshinori Fujimoto

  DOI：10.1248/cpb.54.1473

  日期：——

  The C-24 configuration of (22E,24xi)-24-isopropenyl-22-dehydrocholesterol (1), which was recently isolated from the Colombian Caribbean sponge, Topsentia ophiraphidites, was investigated. Synthesis of the stereodefined (24R)- and (24S)-(22E)-24-isopropenyl-22-dehydrocholesterols (1a, 1b) followed by (1)H- and (13)C-NMR data comparison of these sterols established the (24R)-configuration of 1. In addition

  研究了（22E，24xi）-24-异丙烯基-22-脱氢胆固醇（1）的C-24构型，该构型最近从哥伦比亚加勒比海海绵（Topsentia ophiraphidites）中分离出来。合成立体定义的（24R）-和（24S）-（22E）-24-异丙烯基-22-脱氢胆固醇（1a，1b），然后进行这些固醇的（1）H-和（13）C-NMR数据比较，确定了1.的（24R）-构型。另外，还合成了（24R）-和（24S）-24-异丙烯基胆固醇（2a和2b），并提供了它们的NMR数据。讨论了以前报道的24个异丙烯基胆固醇样品的C-24构型。
• Ophirasterol, a new C31 sterol from the marine sponge Topsentia ophiraphidites
  作者：Gladys J Calderón、Leonardo Castellanos、Carmenza Duque、Shizue Echigo、Noriyuki Hara、Yoshinori Fujimoto

  DOI：10.1016/j.steroids.2003.11.001

  日期：2004.2

  Analysis of the sterol fraction obtained from the Colombian Caribbean sponge Topsentia ophiraphidites revealed that this sponge is a rich source of C-30 and C-31 sterols. Among them, a new C-31 sterol, named ophirasterol, was isolated, and its structure was established as (22E,24R)-24-(1-buten-2-yl)cholesta-5,22-dien-3beta-oI (1) by spectral means and comparison with synthetic C-24 epimers with known configuration. Other isolated C-30 and C-31 sterols were the known 24-ethyl-24-methyl-22-dehydrocholesteroI (2), 24-isopropyl-22-dehydrocholesterol (3), 24-isopropyjcholesterol (4), 24-ethyl-24-methylcholesterol (5), 24-isopropenyl-25-methyl-22-dehydrocholesteroI (6) and 24-isopropenyl-25-methylcholesteroI (7), and 24-isopropenyl-22-dehydrocholesteroI (8). (C) 2003 Elsevier Inc. All rights reserved.