(25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-5α-cholest-16-en-15α-ol | 661460-83-9

• 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: (25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-5α-cholest-16-en-15α-ol
• 英文别名: (3S,5S,8R,9S,10S,13S,14S,15S)-3-[tert-butyl(dimethyl)silyl]oxy-17-[(2R,6R)-7-[tert-butyl(dimethyl)silyl]oxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-15-ol
• CAS: 661460-83-9
• 化学式: C₃₉H₇₄O₃Si₂
• 分子量: 647.186
• InChiKey: HXLHDJSIZMFCQD-SOUHQKFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.39
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  (25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-5α-cholest-16-en-15α-ol 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以98%的产率得到(25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-5α-cholestan-15α-ol
  参考文献：
  名称：

  α-Hydroxylation at C-15 and C-16 in Cholesterol:  Synthesis of (25R)-5α-Cholesta-3β,15α,26-triol and (25R)-5α-Cholesta-3β,16α,26-triol from Diosgenin

  摘要：

  [GRAPHICS](25R)-5alpha-Cholesta-3beta,16alpha,26-triol 7b and (25R)-5alpha-cholesta-3beta,15alpha,26-triol 10b were synthesized, via (25R)-5alpha-cholesta-3beta,16,8,26-triol 5a, from diosgenin 3 in 52% yield over six steps and 47% yield over eight steps, respectively. An efficient method for inversion of a C-16beta hydroxyl to the C-16alpha position and a short method for transposition of a C-16beta hydroxyl to the C-15alpha position via the unexpected beta-reduction of a C-15 ketone in a steroid are reported.

  DOI：

  10.1021/ol036257u
• 作为产物：
  描述：

  薯蓣皂素 在 palladium dihydroxide 吡啶 、 盐酸 、 sodium tetrahydroborate 、 N-羟基丁二酰亚胺 、 sodium dichromate 、 cerium(III) chloride 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 52.5h， 生成 (25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-5α-cholest-16-en-15α-ol
  参考文献：
  名称：

  α-Hydroxylation at C-15 and C-16 in Cholesterol:  Synthesis of (25R)-5α-Cholesta-3β,15α,26-triol and (25R)-5α-Cholesta-3β,16α,26-triol from Diosgenin

  摘要：

  [GRAPHICS](25R)-5alpha-Cholesta-3beta,16alpha,26-triol 7b and (25R)-5alpha-cholesta-3beta,15alpha,26-triol 10b were synthesized, via (25R)-5alpha-cholesta-3beta,16,8,26-triol 5a, from diosgenin 3 in 52% yield over six steps and 47% yield over eight steps, respectively. An efficient method for inversion of a C-16beta hydroxyl to the C-16alpha position and a short method for transposition of a C-16beta hydroxyl to the C-15alpha position via the unexpected beta-reduction of a C-15 ketone in a steroid are reported.

  DOI：

  10.1021/ol036257u

文献信息

• α-Hydroxylation at C-15 and C-16 in Cholesterol:  Synthesis of (25<i>R</i>)-5α-Cholesta-3β,15α,26-triol and (25<i>R</i>)-5α-Cholesta-3β,16α,26-triol from Diosgenin
  作者：John R. Williams、Hua Gong、Nathan Hoff、Olaoluwa I. Olubodun、Patrick J. Carroll

  DOI：10.1021/ol036257u

  日期：2004.1.1

  [GRAPHICS](25R)-5alpha-Cholesta-3beta,16alpha,26-triol 7b and (25R)-5alpha-cholesta-3beta,15alpha,26-triol 10b were synthesized, via (25R)-5alpha-cholesta-3beta,16,8,26-triol 5a, from diosgenin 3 in 52% yield over six steps and 47% yield over eight steps, respectively. An efficient method for inversion of a C-16beta hydroxyl to the C-16alpha position and a short method for transposition of a C-16beta hydroxyl to the C-15alpha position via the unexpected beta-reduction of a C-15 ketone in a steroid are reported.