(1S,2S,4S,5'R,6R,7S,8R,9S,11S,12S,13S,16R,18S)-5',7,9,13-tetramethyl-11,16-bis(phenylmethoxy)spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] | 1246949-31-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,4S,5'R,6R,7S,8R,9S,11S,12S,13S,16R,18S)-5',7,9,13-tetramethyl-11,16-bis(phenylmethoxy)spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]
• CAS: 1246949-31-4
• 化学式: C₄₁H₅₆O₄
• 分子量: 612.893
• InChiKey: GUOPGKZMXUOBSK-HEEHEUKQSA-N

物化性质

• 熔点：
  65-68 °C
• 沸点：
  672.4±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,4S,5'R,6R,7S,8R,9S,11S,12S,13S,16R,18S)-5',7,9,13-tetramethyl-11,16-bis(phenylmethoxy)spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] 在 吡啶盐酸盐 、 二甲基二环氧乙烷 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.5h， 生成
  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：

  龙舌兰皂苷乙酯 在 吡啶 、 甲醇 、 四氧化锇 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 氨 、 sodium hydride 、 calcium 、 potassium carbonate 、 N-甲基吗啉氧化物 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 mineral oil 、 叔丁醇 为溶剂， 反应 32.5h， 生成 (1S,2S,4S,5'R,6R,7S,8R,9S,11S,12S,13S,16R,18S)-5',7,9,13-tetramethyl-11,16-bis(phenylmethoxy)spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]
  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。