diethyl 3α,7α,12α-tris(formyloxy)-5β-cholestan-26,27-dioate | 137813-17-3

• 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: diethyl 3α,7α,12α-tris(formyloxy)-5β-cholestan-26,27-dioate
• 英文别名: diethyl 2-[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-triformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl]propanedioate
• CAS: 137813-17-3
• 化学式: C₃₄H₅₂O₁₀
• 分子量: 620.781
• InChiKey: KCZSXJZAUCKESZ-DUYSEAANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  diethyl 3α,7α,12α-tris(formyloxy)-5β-cholestan-26,27-dioate 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以78%的产率得到3α,7α,12α-trihydroxy-5β-cholestan-26,27-dioic acid
  参考文献：
  名称：

  A convenient synthesis of 5β-cholestan-26-oic and 5β-cholestan-26,27-dioic acids

  摘要：

  A new method for the preparation of 5 beta-cholestan-26-oic acids 7 and their analogs is described. The key steps in the synthesis are: iodination of bis- and tris-formyloxy-5 beta-cholan-24-ols 3; nucleophilic substitution of iodides 4 with diethyl sodiomalonate; complete alkaline hydrolysis of esters 5; and subsequent decarboxylation of geminal diacids 6 in DMSO. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00099-9
• 作为产物：
  描述：

  3α,7α,12α-triformyloxy-5β-cholan-24-ol 在 咪唑 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 diethyl 3α,7α,12α-tris(formyloxy)-5β-cholestan-26,27-dioate
  参考文献：
  名称：

  A convenient synthesis of 5β-cholestan-26-oic and 5β-cholestan-26,27-dioic acids

  摘要：

  A new method for the preparation of 5 beta-cholestan-26-oic acids 7 and their analogs is described. The key steps in the synthesis are: iodination of bis- and tris-formyloxy-5 beta-cholan-24-ols 3; nucleophilic substitution of iodides 4 with diethyl sodiomalonate; complete alkaline hydrolysis of esters 5; and subsequent decarboxylation of geminal diacids 6 in DMSO. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00099-9

文献信息

• A convenient synthesis of 5β-cholestan-26-oic and 5β-cholestan-26,27-dioic acids
  作者：I Starchenkov、P Trapencieris、V Kauss、G Jas、I Kalvinsh

  DOI：10.1016/s0039-128x(99)00099-9

  日期：2000.3

  A new method for the preparation of 5 beta-cholestan-26-oic acids 7 and their analogs is described. The key steps in the synthesis are: iodination of bis- and tris-formyloxy-5 beta-cholan-24-ols 3; nucleophilic substitution of iodides 4 with diethyl sodiomalonate; complete alkaline hydrolysis of esters 5; and subsequent decarboxylation of geminal diacids 6 in DMSO. (C) 2000 Elsevier Science Inc. All rights reserved.