(3R,5R,8R,9S,10S,13R,14S,17R)-17-(5-hydroxypentan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol

• 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,5R,8R,9S,10S,13R,14S,17R)-17-(5-hydroxypentan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 英文别名: (3R,5R,8R,9S,10S,13R,14S,17R)-17-(4-Hydroxy-1-methyl-butyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol；(3R,5R,8R,9S,10S,13R,14S,17R)-17-(5-hydroxypentan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₂₄H₄₂O₂
• 分子量: 362.596
• InChiKey: ACKIMFUPMAASSZ-CVCFKTJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,5R,8R,9S,10S,13R,14S,17R)-17-(5-hydroxypentan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 Phosphoric acid mono-[4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentyl] ester
  参考文献：
  名称：

  Inhibitory potency of lithocholic acid analogs and other bile acids on glucuronosyltransferase activity in a colon cancer cell line

  摘要：

  The effectiveness of analogs of lithocholic acid and other bile acids in inhibiting glucuronosyltransferase activity in a colon cancer cell line was measured in order to identify structural features critical for inhibition of the enzyme. Analogs of lithocholic acid with modifications of the side chain (2-7) were synthesized, in part, to study their inhibitory effects on glucuronosyltransferase activity. Bishomolithocholic acid (4) was synthesized from the iodo derivative (9) by a free radical Michael type reaction using tris(trimethylsilyl)silane as a free radical mediator.

  DOI：

  10.1016/0960-894x(96)00092-3
• 作为产物：
  描述：

  lithocholic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以92 %的产率得到(3R,5R,8R,9S,10S,13R,14S,17R)-17-(5-hydroxypentan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  三苯甲基保护的硫醇和醇的光催化裂解

  摘要：

  我们报告了在 pH 中性条件下三苯甲基硫醚或醚的可见光光催化裂解。该方法导致以中等到极好的收率形成相应的对称二硫化物和醇。该协议只需要添加合适的光催化剂和光使其与多种功能正交，包括酸不稳定保护基团。相同的条件可用于直接将三苯甲基保护的硫醇转化为不对称的二硫化物或硒硫化物，并在固相有机合成中裂解三苯甲基树脂。

  DOI：

  10.1055/a-1979-5933

文献信息

• Carbonyl Compounds by Osmium Tetroxide Oxidation: Preferential Oxidation of Primary over Secondary Hydroxy Groups
  作者：Anna Maria Maione、Aurelio Romeo

  DOI：10.1055/s-1984-31035

  日期：——
• Inhibitory potency of lithocholic acid analogs and other bile acids on glucuronosyltransferase activity in a colon cancer cell line
  作者：H. Schneider、H. Fiander、K.A. Harrison、M. Watson、G.W. Burton、P. Arya

  DOI：10.1016/0960-894x(96)00092-3

  日期：1996.3

  The effectiveness of analogs of lithocholic acid and other bile acids in inhibiting glucuronosyltransferase activity in a colon cancer cell line was measured in order to identify structural features critical for inhibition of the enzyme. Analogs of lithocholic acid with modifications of the side chain (2-7) were synthesized, in part, to study their inhibitory effects on glucuronosyltransferase activity. Bishomolithocholic acid (4) was synthesized from the iodo derivative (9) by a free radical Michael type reaction using tris(trimethylsilyl)silane as a free radical mediator.
• Photocatalytic Cleavage of Trityl Protected Thiols and Alcohols
  作者：Sho Murakami、Cosima Brudy、Bartholomäus Pieber、Moritz Bachmann、Yoshiji Takemoto

  DOI：10.1055/a-1979-5933

  日期：——

  We report the visible light photocatalytic cleavage of trityl thioethers or ethers under pH-neutral conditions. The method results in the formation of the respective symmetrical disulfides and alcohols in moderate to excellent yield. The protocol only requires the addition of a suitable photocatalyst and light rendering it orthogonal to several functionalities, including acid labile protective groups

  我们报告了在 pH 中性条件下三苯甲基硫醚或醚的可见光光催化裂解。该方法导致以中等到极好的收率形成相应的对称二硫化物和醇。该协议只需要添加合适的光催化剂和光使其与多种功能正交，包括酸不稳定保护基团。相同的条件可用于直接将三苯甲基保护的硫醇转化为不对称的二硫化物或硒硫化物，并在固相有机合成中裂解三苯甲基树脂。