4α,24α-dimethyl-5α-cholestan-3β-ol

• 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: 4α,24α-dimethyl-5α-cholestan-3β-ol
• 英文别名: (3S,4S,5S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-4,10,13-trimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₂₉H₅₂O
• 分子量: 416.731
• InChiKey: ATSOHKZZFSOWDR-OBMIQIPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  24β-methylcholesta-4,22E-dien-3-one 在 platinum(IV) oxide potassium tert-butylate 、 氨 、 氢气 、 lithium 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 4α,24α-dimethyl-5α-cholestan-3β-ol
  参考文献：
  名称：

  Marine 4-methyl sterols: Synthesis of C-24 epimers of 4α,24-dimethyl-5α-cholestan-3β-OL and 360 MHz 1HNMR comparisons to the natural product from Plexaura homomalla

  摘要：

  Comparison of the highfield 1HNMR spectrum of 4 alpha, 24-dimethyl-5 alpha-cholestan-3 beta-o1 isolated by open column adsorptive chromatography and reversed-phase HPLC from P. homomalla with those of the corresponding synthetic 24 alpha and 24 beta compounds demonstrate that the gorgonian natural product is purely 24 beta, the same C-24 configuration found in sterols related to dinosterol and gorgosterol. 360 MHz 1HNMR data are also reported for synthetic 4 alpha, 24 beta-dimethyl-5 alpha-cholest-22E-en-3 beta-o1 (another P. homomalla natural product). The use of 1HNMR correlations in assigning C-24 configurations of 24-methyl marine sterols possessing various nuclei is examined and discussed. Analyses of the methyl sterol components of P. homomalla are tabulated and discussed with regard to origin and plausible biosynthetic interrelationships in light of the C-24 configurational findings.

  DOI：

  10.1016/s0039-128x(83)90220-9

文献信息

• Marine 4-methyl sterols: Synthesis of C-24 epimers of 4α,24-dimethyl-5α-cholestan-3β-OL and 360 MHz 1HNMR comparisons to the natural product from Plexaura homomalla
  作者：W.C. Dow、T. Gebreyesus、S. Popov、R.M.K. Carlson、Carl Djerassi

  DOI：10.1016/s0039-128x(83)90220-9

  日期：1983.8

  Comparison of the highfield 1HNMR spectrum of 4 alpha, 24-dimethyl-5 alpha-cholestan-3 beta-o1 isolated by open column adsorptive chromatography and reversed-phase HPLC from P. homomalla with those of the corresponding synthetic 24 alpha and 24 beta compounds demonstrate that the gorgonian natural product is purely 24 beta, the same C-24 configuration found in sterols related to dinosterol and gorgosterol. 360 MHz 1HNMR data are also reported for synthetic 4 alpha, 24 beta-dimethyl-5 alpha-cholest-22E-en-3 beta-o1 (another P. homomalla natural product). The use of 1HNMR correlations in assigning C-24 configurations of 24-methyl marine sterols possessing various nuclei is examined and discussed. Analyses of the methyl sterol components of P. homomalla are tabulated and discussed with regard to origin and plausible biosynthetic interrelationships in light of the C-24 configurational findings.