4-(S)-methanesulfonyloxy-7-trimethylsilanyl-hept-6-ynoic acid methyl ester | 1204182-68-2

• 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: 4-(S)-methanesulfonyloxy-7-trimethylsilanyl-hept-6-ynoic acid methyl ester
• 英文别名: methyl (4S)-4-methylsulfonyloxy-7-trimethylsilylhept-6-ynoate
• CAS: 1204182-68-2
• 化学式: C₁₂H₂₂O₅SSi
• 分子量: 306.455
• InChiKey: VBCZDZOGRHIGGC-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(S)-methanesulfonyloxy-7-trimethylsilanyl-hept-6-ynoic acid methyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以41%的产率得到4-(R)-azido-7-trimethylsilanyl-hept-6-ynoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Azide-Alkyne Fragments for “Click” Chemical Applications. Part 2. Formation of Oligomers from Orthogonally Protected Chiral Trialkylsilylhomopropargyl Azides and Homopropargyl Alcohols

  摘要：

  A small library of chiral, beta(3)-substituted homopropargyl alcohols and chiral beta(3)-substituted trimethylsilylhomopropargyl azides were generated starting from natural L-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding alpha-substituted propargyl alcohols and alpha-substituted trialkylsilylpropargyl azides.

  DOI：

  10.1021/jo9021887
• 作为产物：
  描述：

  甲基磺酰氯 、 4-(S)-hydroxy-7-trimethylsilanyl-hept-6-ynoic acid methyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以92%的产率得到4-(S)-methanesulfonyloxy-7-trimethylsilanyl-hept-6-ynoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Azide-Alkyne Fragments for “Click” Chemical Applications. Part 2. Formation of Oligomers from Orthogonally Protected Chiral Trialkylsilylhomopropargyl Azides and Homopropargyl Alcohols

  摘要：

  A small library of chiral, beta(3)-substituted homopropargyl alcohols and chiral beta(3)-substituted trimethylsilylhomopropargyl azides were generated starting from natural L-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding alpha-substituted propargyl alcohols and alpha-substituted trialkylsilylpropargyl azides.

  DOI：

  10.1021/jo9021887

文献信息

• Synthesis of Azide-Alkyne Fragments for “Click” Chemical Applications. Part 2. Formation of Oligomers from Orthogonally Protected Chiral Trialkylsilylhomopropargyl Azides and Homopropargyl Alcohols
  作者：Oliver D. Montagnat、Guillaume Lessene、Andrew B. Hughes

  DOI：10.1021/jo9021887

  日期：2010.1.15

  A small library of chiral, beta(3)-substituted homopropargyl alcohols and chiral beta(3)-substituted trimethylsilylhomopropargyl azides were generated starting from natural L-amino acids. The free alkynes and azides were then coupled, using a Huisgen 1,3-dipolar cycloaddition, to provide chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as potential peptidomimetic compounds. The work is an extension to the previous synthesis of racemic, orthogonally protected 1,4-disubstituted-1,2,3-triazoles from the corresponding alpha-substituted propargyl alcohols and alpha-substituted trialkylsilylpropargyl azides.