(2R)-2-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one | 1185317-38-7

• 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: (2R)-2-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
• CAS: 1185317-38-7
• 化学式: C₃₄H₅₆O₅Si
• 分子量: 572.901
• InChiKey: ZVDBLBQTEPTLMZ-JRSSDUBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以79%的产率得到pubesenolide
  参考文献：
  名称：

  Synthesis of Sominone and Its Derivatives Based on an RCM Strategy: Discovery of A Novel Anti-Alzheimer’s Disease Medicine Candidate “Denosomin”

  摘要：

  Synthesis of sominone was achieved starting from dehydroepiandrosterone on the basis of an RCM strategy for the construction of a delta-lactone side chain. This synthetic protocol was applied for the synthesis of several analogous derivatives including 1-deoxy-24-norsominone (denosomin), which was revealed to exhibit notable bioactivities for new antidementia chemotherapy, exceeding the original natural compound sominone.

  DOI：

  10.1021/ol901553w
• 作为产物：
  描述：

  [(2S,3R)-2-[(1S,3R,8S,9S,10R,13S,14S,17R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-methylhex-5-en-3-yl] 2-(hydroxymethyl)prop-2-enoate 在 Stewart-Grubbs催化剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以22%的产率得到(2R)-2-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Synthesis of Sominone and Its Derivatives Based on an RCM Strategy: Discovery of A Novel Anti-Alzheimer’s Disease Medicine Candidate “Denosomin”

  摘要：

  Synthesis of sominone was achieved starting from dehydroepiandrosterone on the basis of an RCM strategy for the construction of a delta-lactone side chain. This synthetic protocol was applied for the synthesis of several analogous derivatives including 1-deoxy-24-norsominone (denosomin), which was revealed to exhibit notable bioactivities for new antidementia chemotherapy, exceeding the original natural compound sominone.

  DOI：

  10.1021/ol901553w