methyl (3S)-3-[(E)-but-2-enoxy]-4-[tert-butyl(diphenyl)silyl]oxybutanoate | 713122-71-5

• 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: methyl (3S)-3-[(E)-but-2-enoxy]-4-[tert-butyl(diphenyl)silyl]oxybutanoate
• CAS: 713122-71-5
• 化学式: C₂₅H₃₄O₄Si
• 分子量: 426.628
• InChiKey: KLEIILSKTDLLLP-BXKJMJEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  methyl (3S)-3-[(E)-but-2-enoxy]-4-[tert-butyl(diphenyl)silyl]oxybutanoate 在 potassium trimethylsilonate 作用下， 以 乙醚 为溶剂， 以86%的产率得到(S)-3-[((E)-But-2-enyl)oxy]-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid
  参考文献：
  名称：

  A Concise and Stereoselective Synthesis of the A-Ring Fragment of the Gambieric Acids

  摘要：

  The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations.

  DOI：

  10.1021/ol049483s
• 作为产物：
  描述：

  L-苹果酸二甲酯 在 咪唑 、 sodium tetrahydroborate 、 三氟甲磺酸 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (3S)-3-[(E)-but-2-enoxy]-4-[tert-butyl(diphenyl)silyl]oxybutanoate
  参考文献：
  名称：

  A Concise and Stereoselective Synthesis of the A-Ring Fragment of the Gambieric Acids

  摘要：

  The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations.

  DOI：

  10.1021/ol049483s

文献信息

• A Concise and Stereoselective Synthesis of the A-Ring Fragment of the Gambieric Acids
  作者：J. Stephen Clark、Thomas C. Fessard、Claire Wilson

  DOI：10.1021/ol049483s

  日期：2004.5.1

  The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations.