(1R,2R,4S,8R,10S,14S,17S,18R)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one | 1256561-24-6

• 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: (1R,2R,4S,8R,10S,14S,17S,18R)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one
• CAS: 1256561-24-6
• 化学式: C₃₃H₅₂O₇
• 分子量: 560.772
• InChiKey: WXFMGCVRGSIXOB-UDBYHWGASA-N

物化性质

• 沸点：
  642.3±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  40.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,8R,10S,14S,17S,18R)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one 在 sodium tetrahydroborate 作用下， 生成
  参考文献：
  名称：

  Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone

  摘要：

  9 alpha,14 alpha-epoxy-14-deoxy-20-hydroxyecdysone diacetonideon treatment with NaBH4 undergoes reduction of 6-keto group and cleavage of allylic oxetane ring, the 6-keto reduction is accompanied by beta ->alpha epimerization of the adjacent HC5 centre. Subsequent re-oxidation of the 6-CHOH fragment into ketone with pyridinium chlorochromate and acidic deprotection affords 25-hydroxydachryhainansterone possessing beta-HC5 configuration due to the re-epimerisation at this centre

  DOI：

  10.1016/j.mencom.2010.09.019
• 作为产物：
  描述：

  脱皮甾酮 2,3:20,22-二缩丙酮 在 sodium hydroxide 作用下， 反应 24.0h， 生成 (1R,2R,4S,8R,10S,14S,17S,18R)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one
  参考文献：
  名称：

  Hydroxylation and epimerization of ecdysteroids in alkaline media: Stereoselective synthesis of 9α-hydroxy-5α-ecdysteroids

  摘要：

  Autoxidation of diacetonides of 20-hydroxyecdysone and ponasterone A under treatment with excess of NaOH in methanol leads to the formation of 9α-hydroxy-5α-ecdysteroids previously not described. Their structures have been determined by detailed NMR analysis. Catalytic hydrogenation (Pd-C, MeOH-MeONa) of hydroxylated ecdysteroids affords the 7,8α-dihydro-9α-hydroxy-5α-ecdysteroids.

  DOI：

  10.1016/j.steroids.2014.06.019