3β,4β-Isopropylidendioxy-5α-cholestanol-(5) | 104377-37-9

• 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: 3β,4β-Isopropylidendioxy-5α-cholestanol-(5)
• 英文别名: (1S,2R,5S,9S,10S,13S,14S,17R,18R)-2,7,7,18-tetramethyl-17-[(2R)-6-methylheptan-2-yl]-6,8-dioxapentacyclo[11.7.0.02,10.05,9.014,18]icosan-10-ol
• CAS: 104377-37-9
• 化学式: C₃₀H₅₂O₃
• 分子量: 460.741
• InChiKey: KSKCWHFYKVFCKU-KUKCXLQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4,5)β-epoxy-5β-cholestan-3β-ol 在 高氯酸 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3β,4β-Isopropylidendioxy-5α-cholestanol-(5)
  参考文献：
  名称：

  Atypical regioselective biohydrolysis on steroidal oxiranes by Aspergillus niger whole cells: Some stereochemical features

  摘要：

  5,6-Epoxycholestan-3 beta-ol derivatives were hydrolyzed in a diastereoconvergent manner by growing and resting cells of several strains of Aspergillus niger, particularly A. niger ATCC 11394. These strains displayed opposite regioselectivity toward each isomer in an a and P epoxide mixture, thus, the nucleophilic attack took place at the less substituted and the most substituted carbon atom on each diasteromer, respectively These biocatalysts opened trisubstituted oxiranes but were unable to hydrolyze the disubstituted oxiranes in the tested sterol derivatives. These findings suggest that A. niger strains possess another hydrolytic ability different from the commercial A. niger epoxide hydrolase (EH) that did not accept this kind of steroidal oxiranes as substrates. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.04.003