[(2R,6R)-6-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-[2-(4-benzoylphenyl)acetyl]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]-2-methylheptyl] 2,2-dimethylpropanoate | 894357-60-9

• 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: [(2R,6R)-6-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-[2-(4-benzoylphenyl)acetyl]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]-2-methylheptyl] 2,2-dimethylpropanoate
• CAS: 894357-60-9
• 化学式: C₄₇H₆₆O₅
• 分子量: 711.038
• InChiKey: KWTHSXWZCBRLAM-JWDYGNTESA-N

物化性质

• 沸点：
  732.1±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,6R)-6-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-[2-(4-benzoylphenyl)acetyl]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]-2-methylheptyl] 2,2-dimethylpropanoate 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.5h， 生成 (25R)-5α-cholestane-3α,15α,26-triol
  参考文献：
  名称：

  Synthesis of the Aglycone of the Shark Repellent Pavoninin-4 Using Remote Functionalization

  摘要：

  The aglycone of shark repellent pavoninin-4, (25R)-5 alpha-cholestan-3 alpha,15 alpha,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3 beta,-26-diol 4(26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy was used as a key step to introduce the C-15 alpha alcohol on a steroid D ring. An efficient synthesis of the 26-hydroxycholesterol from the 16 beta hydroxyl steroid, (25R)cholest-5-ene-3 beta,16 beta,26-triol (3a), is also reported.

  DOI：

  10.1021/ol060079y
• 作为产物：
  描述：

  在 钯 lithium aluminium tetrahydride 、 氢气 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 [(2R,6R)-6-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-[2-(4-benzoylphenyl)acetyl]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]-2-methylheptyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis of the Aglycone of the Shark Repellent Pavoninin-4 Using Remote Functionalization

  摘要：

  The aglycone of shark repellent pavoninin-4, (25R)-5 alpha-cholestan-3 alpha,15 alpha,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3 beta,-26-diol 4(26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy was used as a key step to introduce the C-15 alpha alcohol on a steroid D ring. An efficient synthesis of the 26-hydroxycholesterol from the 16 beta hydroxyl steroid, (25R)cholest-5-ene-3 beta,16 beta,26-triol (3a), is also reported.

  DOI：

  10.1021/ol060079y

文献信息

• Synthesis of the Aglycone of the Shark Repellent Pavoninin-4 Using Remote Functionalization
  作者：Hua Gong、John R. Williams

  DOI：10.1021/ol060079y

  日期：2006.5.1

  The aglycone of shark repellent pavoninin-4, (25R)-5 alpha-cholestan-3 alpha,15 alpha,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3 beta,-26-diol 4(26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy was used as a key step to introduce the C-15 alpha alcohol on a steroid D ring. An efficient synthesis of the 26-hydroxycholesterol from the 16 beta hydroxyl steroid, (25R)cholest-5-ene-3 beta,16 beta,26-triol (3a), is also reported.