(20R,22R)-3β-tert-butyldimethylsiloxy-20-hydroxy-22,25-epoxy-25-homo-5α-cholane | 205368-94-1

• 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: (20R,22R)-3β-tert-butyldimethylsiloxy-20-hydroxy-22,25-epoxy-25-homo-5α-cholane
• 英文别名: (1R)-1-[(3S,5S,8R,9S,10S,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-[(2R)-oxolan-2-yl]ethanol
• CAS: 205368-94-1
• 化学式: C₃₁H₅₆O₃Si
• 分子量: 504.869
• InChiKey: MISRHMMYDSECDZ-NPCSOTFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  35
• 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

• 作为反应物：
  描述：

  (20R,22R)-3β-tert-butyldimethylsiloxy-20-hydroxy-22,25-epoxy-25-homo-5α-cholane 在 2,6-二甲基吡啶 、 ruthenium(IV) oxide 、 sodium periodate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 28.0h， 生成 (20R,22R)-5α-cholestane-3β,20,22,25-tetraol
  参考文献：
  名称：

  Alternative Access to 20-Hydroxyecdysteroid Side Chain by Means of Samarium Iodide-promoted Radical Addition of Tetrahydrofuran to a 20-Keto Steroid

  摘要：

  Samarium iodide-promoted radical addition of tetrahydrofuran to the 20-keto steroid afforded the adducts as a mixture of diastereomers at the 22-position in high yield. Both adducts were further converted into (20R,22R)-5 alpha-cholestane-3 beta,20,22,25-tetraol.

  DOI：

  10.3987/com-97-s(n)83
• 作为产物：
  描述：

  四氢呋喃 、 5α-pregnan-20-one tert-butyldimethylsilyl ether 在 samarium diiodide 、 碘苯 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 0.08h， 以46.3%的产率得到(20R,22R)-3β-tert-butyldimethylsiloxy-20-hydroxy-22,25-epoxy-25-homo-5α-cholane
  参考文献：
  名称：

  Alternative Access to 20-Hydroxyecdysteroid Side Chain by Means of Samarium Iodide-promoted Radical Addition of Tetrahydrofuran to a 20-Keto Steroid

  摘要：

  Samarium iodide-promoted radical addition of tetrahydrofuran to the 20-keto steroid afforded the adducts as a mixture of diastereomers at the 22-position in high yield. Both adducts were further converted into (20R,22R)-5 alpha-cholestane-3 beta,20,22,25-tetraol.

  DOI：

  10.3987/com-97-s(n)83

文献信息

• Alternative Access to 20-Hydroxyecdysteroid Side Chain by Means of Samarium Iodide-promoted Radical Addition of Tetrahydrofuran to a 20-Keto Steroid
  作者：Toshio Honda、Miho Katoh

  DOI：10.3987/com-97-s(n)83

  日期：——

  Samarium iodide-promoted radical addition of tetrahydrofuran to the 20-keto steroid afforded the adducts as a mixture of diastereomers at the 22-position in high yield. Both adducts were further converted into (20R,22R)-5 alpha-cholestane-3 beta,20,22,25-tetraol.