(3beta,5alpha,6beta,20S)-6-Methoxy-3,5-cyclopregnane-20-methanol

• 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: (3beta,5alpha,6beta,20S)-6-Methoxy-3,5-cyclopregnane-20-methanol
• 英文别名: 2-(8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl)propan-1-ol
• 化学式: C₂₃H₃₈O₂
• 分子量: 346.5
• InChiKey: FHAMDNXTPYSJGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

文献信息

• [EN] NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL<br/>[FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE DE 25-OH CHOLESTÉROL/CALCIFÉDIOL À PARTIR DE PHYTOSTÉROL
  申请人：FERMENTA BIOTECH LTD

  公开号：WO2020225830A1

  公开（公告）日：2020-11-12

  The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy] butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3(Calcifediol) in good yield.

  本发明揭示了一种从廉价的原始植物甾醇合成素食25-OH胆固醇/钙化二醇的新方法。根据该方法，通过对烷基化和甲醇化反应形成相应的i-类固醇。i-类固醇通过还原臭氧化反应生成C-22醇，并通过C-22烷基磺酸酯转化为C-22碘化物，收率良好。将C-22烷基磺酸酯与4-溴-2-甲基-2-[(三甲基硅基)氧基]丁烷的Grignard试剂偶联，然后去保护基，得到25-OH胆固醇。在一个过程变体中，通过镍介导的C-22碘化物与电子亏损的烯烃乙基丙烯酸酯进行共轭加成，然后用甲基镁溴化物处理相应的酯，以高收率安装25-OH胆固醇的侧链。进一步，对25-OH胆固醇二乙酸酯进行溴化反应，随后使用TBAF进行脱溴反应，得到25-OH 7-脱氢胆固醇。进一步，将25-OH 7-脱氢胆固醇进行光反应，使用高压或中压汞灯，然后将previtamin D3进行热反应，得到25-OH维生素D3（钙化二醇），收率良好。
• NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL
  申请人：FERMENTA BIOTECH LIMITED

  公开号：US20220204547A1

  公开（公告）日：2022-06-30

  The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy]butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3 (Calcifediol) in good yield.