ethyl (2S)-2-acetamido-3-[4-(2,2-dimethylpropoxysulfonylmethyl)phenyl]propanoate | 1146758-13-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2S)-2-acetamido-3-[4-(2,2-dimethylpropoxysulfonylmethyl)phenyl]propanoate
• CAS: 1146758-13-5
• 化学式: C₁₉H₂₉NO₆S
• 分子量: 399.508
• InChiKey: IOLZJYYHNNRAKB-KRWDZBQOSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  593.6±50.0 °C(predicted)
• 密度：
  1.172±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (2S)-2-acetamido-3-[4-(chlorosulfonylmethyl)phenyl]propanoate 、 新戊醇 在 2,6-二甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (2S)-2-acetamido-3-[4-(2,2-dimethylpropoxysulfonylmethyl)phenyl]propanoate
  参考文献：
  名称：

  Trichloroethyl Group As a Protecting Group for Sulfonates and Its Application to the Synthesis of a Disulfonate Analog of the Tyrosine Sulfated PSGL-1₄₃₋₅₀ Peptide

  摘要：

  The trichloroethyl (TCE) group is shown to be a viable protecting group for sulfonates. TCE-protected sulfonates were found to be particularly stable to acid, a key characteristic that led to a straightforward enantioselective synthesis of L-FmocPhe(p-CH2SO3TCE)OH. This was used as a building block for the solid phase synthesis of an octapeptide corresponding to P-selectin glycoprotein ligand-1 residues 43-50 (PSGL-1(43-50)) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.

  DOI：

  10.1021/jo900122c

文献信息

• Trichloroethyl Group As a Protecting Group for Sulfonates and Its Application to the Synthesis of a Disulfonate Analog of the Tyrosine Sulfated PSGL-1₄₃₋₅₀ Peptide
  作者：Ahmed M. Ali、Bryan Hill、Scott D. Taylor

  DOI：10.1021/jo900122c

  日期：2009.5.1

  The trichloroethyl (TCE) group is shown to be a viable protecting group for sulfonates. TCE-protected sulfonates were found to be particularly stable to acid, a key characteristic that led to a straightforward enantioselective synthesis of L-FmocPhe(p-CH2SO3TCE)OH. This was used as a building block for the solid phase synthesis of an octapeptide corresponding to P-selectin glycoprotein ligand-1 residues 43-50 (PSGL-1(43-50)) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.