methyl 3-[[[(2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-(4-prop-2-enoxyphenyl)propanoyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]-5-(bromomethyl)benzoate | 147363-14-2

• 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: methyl 3-[[[(2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-(4-prop-2-enoxyphenyl)propanoyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]-5-(bromomethyl)benzoate
• CAS: 147363-14-2
• 化学式: C₃₇H₄₉BrN₂O₁₀
• 分子量: 761.707
• InChiKey: RPXGMXQEJLFHQX-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  50
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 3-[[[(2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-(4-prop-2-enoxyphenyl)propanoyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]-5-(bromomethyl)benzoate 在 甲醇 、 potassium carbonate 、 乙酰氯 作用下， 反应 3.5h， 生成 methyl O-allyl-L-tyrosinate
  参考文献：
  名称：

  Practical synthesis of a highly enantioselective receptor for peptides

  摘要：

  A practical synthesis of a highly enantioselective, C3-symmetric host molecule (2) has been developed. The basic strategy is a significant improvement over the relatively lengthy previous synthesis and involves direct addition of a Boc-tyrosine amide anion derivative 4 to methyl 3,5-bis(bromomethyl)-benzoate to give an advanced intermediate (5). The final step, a triple macrolactamization, closes three 19-membered rings simultaneously to produce the bridged macrotricyclic receptor in 70-80% yield.

  DOI：

  10.1021/jo00058a005
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 四丁基碘化铵 4-二甲氨基吡啶 、 氨 、 sodium hexamethyldisilazane 、 四丁基碘化铵 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.83h， 生成 methyl 3-[[[(2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-(4-prop-2-enoxyphenyl)propanoyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]-5-(bromomethyl)benzoate
  参考文献：
  名称：

  Practical synthesis of a highly enantioselective receptor for peptides

  摘要：

  A practical synthesis of a highly enantioselective, C3-symmetric host molecule (2) has been developed. The basic strategy is a significant improvement over the relatively lengthy previous synthesis and involves direct addition of a Boc-tyrosine amide anion derivative 4 to methyl 3,5-bis(bromomethyl)-benzoate to give an advanced intermediate (5). The final step, a triple macrolactamization, closes three 19-membered rings simultaneously to produce the bridged macrotricyclic receptor in 70-80% yield.

  DOI：

  10.1021/jo00058a005

文献信息

• Practical synthesis of a highly enantioselective receptor for peptides
  作者：Shawn D. Erickson、Julian A. Simon、W. Clark Still

  DOI：10.1021/jo00058a005

  日期：1993.3

  A practical synthesis of a highly enantioselective, C3-symmetric host molecule (2) has been developed. The basic strategy is a significant improvement over the relatively lengthy previous synthesis and involves direct addition of a Boc-tyrosine amide anion derivative 4 to methyl 3,5-bis(bromomethyl)-benzoate to give an advanced intermediate (5). The final step, a triple macrolactamization, closes three 19-membered rings simultaneously to produce the bridged macrotricyclic receptor in 70-80% yield.