ethyl (2R,3S)-2,3-bis(tert-butyldimethylsilyloxy)octanoate | 1156535-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2R,3S)-2,3-bis(tert-butyldimethylsilyloxy)octanoate
• 英文别名: ethyl (2R,3S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]octanoate
• CAS: 1156535-96-4
• 化学式: C₂₂H₄₈O₄Si₂
• 分子量: 432.792
• InChiKey: OICTWHTVQKMWFR-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2R,3S)-2,3-bis(tert-butyldimethylsilyloxy)octanoate 在 二异丁基氢化铝 、 potassium tartrate sodium salt 、 水 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以96%的产率得到(2S,3S)-2,3-bis(tert-butyldimethylsilyloxy)-1-octanol
  参考文献：
  名称：

  A concise synthesis of pinellic acid using a cross-metathesis approach

  摘要：

  A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. This synthesis is the shortest to date, furnishing pinellic acid in 17% overall yield via only seven steps from a readily available known dihydroxy ester. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.063
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 ethyl 2,3-dihydroxyoctanoate 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到ethyl (2R,3S)-2,3-bis(tert-butyldimethylsilyloxy)octanoate
  参考文献：
  名称：

  A concise synthesis of pinellic acid using a cross-metathesis approach

  摘要：

  A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. This synthesis is the shortest to date, furnishing pinellic acid in 17% overall yield via only seven steps from a readily available known dihydroxy ester. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.063

文献信息

• A concise synthesis of pinellic acid using a cross-metathesis approach
  作者：Ayako Miura、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2009.02.063

  日期：2009.4

  A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. This synthesis is the shortest to date, furnishing pinellic acid in 17% overall yield via only seven steps from a readily available known dihydroxy ester. (C) 2009 Elsevier Ltd. All rights reserved.