methyl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-9-(((tert-butyldimethylsilyl)oxy)methyl)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate | 1100749-69-6

• 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: methyl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-9-(((tert-butyldimethylsilyl)oxy)methyl)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
• CAS: 1100749-69-6
• 化学式: C₃₇H₆₄O₄Si
• 分子量: 600.998
• InChiKey: LEHUWDUGIMCOJY-NJDIOTJMSA-N

物化性质

• 沸点：
  593.3±50.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.32
• 重原子数：
  42.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-9-(((tert-butyldimethylsilyl)oxy)methyl)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以78%的产率得到methyl 23-O-tert-butyldimethylsilyl-3-oxoolean-12-en-28-oate
  参考文献：
  名称：

  Chemical modifications of natural triterpenes—glycyrrhetinic and boswellic acids: evaluation of their biological activity

  摘要：

  Synthetic analogues of naturally occurring triterpenoids: glycyrrhetinic acid, arjunolic acid, and boswellic acids, by modification of A-ring with a cyano- and enone-functionality, have been reported. A novel method of synthesis of alpha-cyanoenones from isoxazoles is reported. Bioassays using primary mouse macrophages and tumor cell lines indicate potent anti-inflammatory and cycotoxic activities associated with cyano-enones of boswellic acid and glycyrrhetinic acid. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tet.2008.10.035
• 作为产物：
  描述：

  methyl hederageninate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以91%的产率得到methyl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-9-(((tert-butyldimethylsilyl)oxy)methyl)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
  参考文献：
  名称：

  Chemical modifications of natural triterpenes—glycyrrhetinic and boswellic acids: evaluation of their biological activity

  摘要：

  Synthetic analogues of naturally occurring triterpenoids: glycyrrhetinic acid, arjunolic acid, and boswellic acids, by modification of A-ring with a cyano- and enone-functionality, have been reported. A novel method of synthesis of alpha-cyanoenones from isoxazoles is reported. Bioassays using primary mouse macrophages and tumor cell lines indicate potent anti-inflammatory and cycotoxic activities associated with cyano-enones of boswellic acid and glycyrrhetinic acid. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tet.2008.10.035