3,6-dimethoxymethyl-3α,6α,24-trihydroxy-5β-cholane | 150933-61-2

• 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: 3,6-dimethoxymethyl-3α,6α,24-trihydroxy-5β-cholane
• 英文别名: (4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-bis(methoxymethoxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentan-1-ol
• CAS: 150933-61-2
• 化学式: C₂₈H₅₀O₅
• 分子量: 466.702
• InChiKey: BBOPKYCMERWUML-HYENIYGMSA-N

物化性质

• 沸点：
  523.7±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-dimethoxymethyl-3α,6α,24-trihydroxy-5β-cholane 在 正丁基锂 、 草酰氯 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 14.5h， 生成 Δ²⁴-3α,6α-dihydroxy-5β-cholestene
  参考文献：
  名称：

  A new highly stereoselective synthesis of cerebrosterol, an agonist of the nuclear receptor LXRs

  摘要：

  The title compound, cerebrosterol 1, was synthesized stereoselectively (97% d.e.) in 41% overall yield from methyl hyodeoxycholanate 2 in 10 steps with desmosterol acetate 8 as the key intermediate and the modified Sharpless asymmetric dihydroxylation as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00812-2
• 作为产物：
  描述：

  methyl 3α,6α-di(methoxymethyl)hyodeoxycholate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以94%的产率得到3,6-dimethoxymethyl-3α,6α,24-trihydroxy-5β-cholane
  参考文献：
  名称：

  A new highly stereoselective synthesis of cerebrosterol, an agonist of the nuclear receptor LXRs

  摘要：

  The title compound, cerebrosterol 1, was synthesized stereoselectively (97% d.e.) in 41% overall yield from methyl hyodeoxycholanate 2 in 10 steps with desmosterol acetate 8 as the key intermediate and the modified Sharpless asymmetric dihydroxylation as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00812-2

文献信息

• A new highly stereoselective synthesis of cerebrosterol, an agonist of the nuclear receptor LXRs
  作者：Xiang-Dong Zhou、Wei-Shan Zhou

  DOI：10.1016/s0040-4020(01)00812-2

  日期：2001.9

  The title compound, cerebrosterol 1, was synthesized stereoselectively (97% d.e.) in 41% overall yield from methyl hyodeoxycholanate 2 in 10 steps with desmosterol acetate 8 as the key intermediate and the modified Sharpless asymmetric dihydroxylation as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.