ethyl (2E,5S,7R)-7-[(2E,5R)-5-(tert-butyldimethylsiloxy)hex-2-enoyloxy]-5-(methoxymethoxy)oct-2-enoate | 1232683-01-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2E,5S,7R)-7-[(2E,5R)-5-(tert-butyldimethylsiloxy)hex-2-enoyloxy]-5-(methoxymethoxy)oct-2-enoate
• 英文别名: ethyl (E,5S,7R)-7-[(E,5R)-5-[tert-butyl(dimethyl)silyl]oxyhex-2-enoyl]oxy-5-(methoxymethoxy)oct-2-enoate
• CAS: 1232683-01-0
• 化学式: C₂₄H₄₄O₇Si
• 分子量: 472.695
• InChiKey: LFMQGYHEWUJOQM-SNHYNKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (2E,5S,7R)-7-[(2E,5R)-5-(tert-butyldimethylsiloxy)hex-2-enoyloxy]-5-(methoxymethoxy)oct-2-enoate 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以86%的产率得到ethyl (2E,5S,7R)-7-[(2E,5R)-5-hydroxyhex-2-enoyloxy]-5-(methoxymethoxy)oct-2-enoate
  参考文献：
  名称：

  Stereoselective Total Synthesis of (-)-Colletol by Prins Cyclisation

  摘要：

  A simple and efficient asymmetric total synthesis of the bis-macrolactone (-)-colletol was accomplished, proving the versatility of the Prins cyclisation in natural product synthesis. The synthesis mainly relies upon reductive opening of a pyran ring, Mitsunobu inversion, the Wittig reaction, and Yamaguchi macrolactonisation as the key steps.

  DOI：

  10.1055/s-0029-1218679
• 作为产物：
  描述：

  ethyl (2E,5S,7S)-7-hydroxy-5-(methoxymethoxy)oct-2-enoate 、 (2E,5S)-5-t-butyldimethylsiloxy-2-hexenoic acid 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到ethyl (2E,5S,7R)-7-[(2E,5R)-5-(tert-butyldimethylsiloxy)hex-2-enoyloxy]-5-(methoxymethoxy)oct-2-enoate
  参考文献：
  名称：

  Stereoselective Total Synthesis of (-)-Colletol by Prins Cyclisation

  摘要：

  A simple and efficient asymmetric total synthesis of the bis-macrolactone (-)-colletol was accomplished, proving the versatility of the Prins cyclisation in natural product synthesis. The synthesis mainly relies upon reductive opening of a pyran ring, Mitsunobu inversion, the Wittig reaction, and Yamaguchi macrolactonisation as the key steps.

  DOI：

  10.1055/s-0029-1218679

文献信息

• Stereoselective Total Synthesis of (-)-Colletol by Prins Cyclisation
  作者：Jhillu Yadav、N. Reddy、P. Reddy、Hissana Ather、Attaluri Prasad

  DOI：10.1055/s-0029-1218679

  日期：2010.5

  A simple and efficient asymmetric total synthesis of the bis-macrolactone (-)-colletol was accomplished, proving the versatility of the Prins cyclisation in natural product synthesis. The synthesis mainly relies upon reductive opening of a pyran ring, Mitsunobu inversion, the Wittig reaction, and Yamaguchi macrolactonisation as the key steps.