(25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-cholest-5-en-16β-ol-16-acetate | 561301-37-9

• 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: (25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-cholest-5-en-16β-ol-16-acetate
• 英文别名: [(3S,8S,9S,10R,13S,14S,16S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-17-[(2R,6R)-7-[tert-butyl(dimethyl)silyl]oxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
• CAS: 561301-37-9
• 化学式: C₄₁H₇₆O₄Si₂
• 分子量: 689.223
• InChiKey: IBRWTXRDIOBDDS-WIXOQPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.96
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-cholest-5-en-16β-ol-16-acetate 反应 0.5h， 以89%的产率得到(25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-cholesta-5,15-diene
  参考文献：
  名称：

  Synthesis of the aglycone of 26-O-deacetyl pavoninin-5

  摘要：

  The aglycone of 26-O-deacetyl pavoninin-5, (25R)-cholest-5-en-3beta,15alpha,26-triol, 5a, was synthesized in 10 steps in 17% overall yield from diosgenin, 3. Removing mercury from the Clemmensen reduction of diosgenin 3, gave a higher yield of (25R)-cholest-5-en-3beta,16beta,26-triol, 4, by a method, that is also more environmentally friendly. Attempted methods for the transposition of the C-16beta hydroxyl to the 15alpha position are described. A successful method for this transposition via the 15alpha-hydroxy-16-ketone, 13, using the Barton deoxygenation reaction on the 16-alcohol, 15, is reported. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00260-6
• 作为产物：
  描述：

  (25R)-cholest-5-en-3β,16β,26-triol 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 34.0h， 生成 (25R)-3β,26-bis[(tert-butyldimethylsilyl)oxy]-cholest-5-en-16β-ol-16-acetate
  参考文献：
  名称：

  Synthesis of the aglycone of 26-O-deacetyl pavoninin-5

  摘要：

  The aglycone of 26-O-deacetyl pavoninin-5, (25R)-cholest-5-en-3beta,15alpha,26-triol, 5a, was synthesized in 10 steps in 17% overall yield from diosgenin, 3. Removing mercury from the Clemmensen reduction of diosgenin 3, gave a higher yield of (25R)-cholest-5-en-3beta,16beta,26-triol, 4, by a method, that is also more environmentally friendly. Attempted methods for the transposition of the C-16beta hydroxyl to the 15alpha position are described. A successful method for this transposition via the 15alpha-hydroxy-16-ketone, 13, using the Barton deoxygenation reaction on the 16-alcohol, 15, is reported. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00260-6