(3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-[(2R,5S)-2-hydroxy-5,6-dimethyl-6-(oxan-2-yloxy)hept-3-yn-2-yl]-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-ol | 1246949-28-9

• 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,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-[(2R,5S)-2-hydroxy-5,6-dimethyl-6-(oxan-2-yloxy)hept-3-yn-2-yl]-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-ol
• CAS: 1246949-28-9
• 化学式: C₄₇H₆₆O₆
• 分子量: 727.037
• InChiKey: NRJKRUFJPNMBRK-OMRHLYDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  53
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-[(2R,5S)-2-hydroxy-5,6-dimethyl-6-(oxan-2-yloxy)hept-3-yn-2-yl]-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-ol 在 氨 、 水 、 lithium 、 mercuric triflate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.17h， 生成 (3α,5α,11β,17ξ,22S,24S)-24-methyl-22,25-epoxyfurostan-3,11,20-triol
  参考文献：
  名称：

  Synthesis of the Antiproliferative Agent Hippuristanol and Its Analogues via Suárez Cyclizations and Hg(II)-Catalyzed Spiroketalizations

  摘要：

  A full account of the synthesis of hippuristanol and its analogues is described. Hecogenin acetate was identified as a suitable and economical starting material for this work, and substrate-controlled stereo-selection was obtained throughout the construction of the key spiroketal unit. Suarez cyclization was first used, but Hg(II)-catalyzed spiroketalization of the 3-alkyne-1,7-diol motif was finally identified as the most convenient strategy.

  DOI：

  10.1021/jo102054r
• 作为产物：
  描述：

  (3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-3,11-bis(benzyloxy)-17-(2-hydroxybut-3-en-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-16-ol 在 sodium periodate 、 四氧化锇 、 正丁基锂 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 15.75h， 生成 (3R,5S,8S,9S,10S,11S,13S,14S,16S,17R)-17-[(2R,5S)-2-hydroxy-5,6-dimethyl-6-(oxan-2-yloxy)hept-3-yn-2-yl]-10,13-dimethyl-3,11-bis(phenylmethoxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-ol
  参考文献：
  名称：

  Synthesis of the Antiproliferative Agent Hippuristanol and Its Analogues via Suárez Cyclizations and Hg(II)-Catalyzed Spiroketalizations

  摘要：

  A full account of the synthesis of hippuristanol and its analogues is described. Hecogenin acetate was identified as a suitable and economical starting material for this work, and substrate-controlled stereo-selection was obtained throughout the construction of the key spiroketal unit. Suarez cyclization was first used, but Hg(II)-catalyzed spiroketalization of the 3-alkyne-1,7-diol motif was finally identified as the most convenient strategy.

  DOI：

  10.1021/jo102054r

文献信息

• Efficient Synthetic Approach to Potent Antiproliferative Agent Hippuristanol via Hg(II)-Catalyzed Spiroketalization
  作者：Kontham Ravindar、Maddi Sridhar Reddy、Lisa Lindqvist、Jerry Pelletier、Pierre Deslongchamps

  DOI：10.1021/ol1019663

  日期：2010.10.1

  The steroidal natural product hippuristanol targets eukaryotic translation initiation factor (eIF)4A which plays a pivotal role in translation in eukaryotic cells. Now an efficient synthesis of hippuristanol from 11-ketotigogenin is reported. The synthesis features a rapid construction of a spiroketal unit via Hg(OTf)2-catalyzed oxidation/spiroketalization of the 3-alkyn-1,7-diol motif.

  类固醇天然产物hippuristanol靶向真核翻译起始因子（eIF）4A，该因子在真核细胞的翻译中起关键作用。现在已经报道了由11-酮基生成素有效合成马尿嘌呤醇。该合成的特征是通过Hg（OTf）2催化3-炔基1,7-二醇基序的氧化/螺缩酮化作用来快速构建螺缩酮单元。