methyl 3α-(ethoxycarbonyloxy)-7α-(trimethlsilyloxy)-5β-cholanoate | 1115381-94-6

• 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: methyl 3α-(ethoxycarbonyloxy)-7α-(trimethlsilyloxy)-5β-cholanoate
• CAS: 1115381-94-6
• 化学式: C₃₁H₅₄O₆Si
• 分子量: 550.852
• InChiKey: REFSQFGJPMUUIE-PTUOMBSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3α-(ethoxycarbonyloxy)-7α-(trimethlsilyloxy)-5β-cholanoate 、 二氧化碳 、 3-溴丙烯 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 以30%的产率得到methyl 3α-(ethoxycarbonyloxy)-7α-(allyloxycarbonyloxy)-5β-cholanoate
  参考文献：
  名称：

  Synthesis and comparative spectroscopic analysis of two chenodeoxycholic acid (CDCA) derivatives with closely related 7α-ester moieties

  摘要：

  3 alpha-Hydroxyl-7 alpha-(4-pentenoyloxy)-5 beta-cholanoic acid (5) has been synthesized in four step reactions starting from CDCA. The serendipitous synthesis of methyl 3 alpha-(allyloxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate (7) has led us to compare the spectroscopic difference of the 7 alpha-(allyloxycarbonyloxy)group versus the 7 alpha-(4-pentenoyloxy) group. The molecular Structures of these compounds were confirmed by X-ray Crystallography. Methyl 3 alpha-(ethoxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate was obtained by a method, which may prove useful in the synthesis of C-14-labeled derivatives for metabolic studies. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.052
• 作为产物：
  描述：

  三甲基氯硅烷 、 (3alpha,5beta,7alpha)-3-[(乙氧羰基)氧基]-7-羟基胆烷-24-酸甲酯 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以95%的产率得到methyl 3α-(ethoxycarbonyloxy)-7α-(trimethlsilyloxy)-5β-cholanoate
  参考文献：
  名称：

  Synthesis and comparative spectroscopic analysis of two chenodeoxycholic acid (CDCA) derivatives with closely related 7α-ester moieties

  摘要：

  3 alpha-Hydroxyl-7 alpha-(4-pentenoyloxy)-5 beta-cholanoic acid (5) has been synthesized in four step reactions starting from CDCA. The serendipitous synthesis of methyl 3 alpha-(allyloxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate (7) has led us to compare the spectroscopic difference of the 7 alpha-(allyloxycarbonyloxy)group versus the 7 alpha-(4-pentenoyloxy) group. The molecular Structures of these compounds were confirmed by X-ray Crystallography. Methyl 3 alpha-(ethoxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate was obtained by a method, which may prove useful in the synthesis of C-14-labeled derivatives for metabolic studies. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.052