(E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid | 151133-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid
• 英文别名: (E,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[4-tri(propan-2-yl)silyloxyphenyl]pent-2-enoic acid
• CAS: 151133-12-9
• 化学式: C₂₅H₄₁NO₅Si
• 分子量: 463.69
• InChiKey: JGYUORQKOSMVCW-FFXXTYGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid 在 四(三苯基膦)钯 N-甲基吗啉 、 5,5-二甲基-1,3-环己二酮 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Total synthesis of cyclotheonamide A

  摘要：

  The potent serine protease inhibitor cyclotheonamide A was prepared in a convergent strategy from D-phenylalanine (D-Phe), vinylogous L-tyrosine (L-Vty), L-diaminopropanoic acid (L-Dpr), L-proline (L-Pro), and a hydroxy acid derivative of L-arginine. Macrocyclic ring closure between the D-Phe and the L-Vty residues was performed via the pentafluorophenyl ester, and the Dess-Martin periodinane was used for the oxidation of the hydroxyamide to the alpha-ketoarginine (L-Kar) residue.

  DOI：

  10.1021/jo00073a010
• 作为产物：
  描述：

  Boc-Tyr-Weinreb amide 在 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-(S)-4-tert-Butoxycarbonylamino-5-(4-triisopropylsilanyloxy-phenyl)-pent-2-enoic acid
  参考文献：
  名称：

  Total synthesis of cyclotheonamide A

  摘要：

  The potent serine protease inhibitor cyclotheonamide A was prepared in a convergent strategy from D-phenylalanine (D-Phe), vinylogous L-tyrosine (L-Vty), L-diaminopropanoic acid (L-Dpr), L-proline (L-Pro), and a hydroxy acid derivative of L-arginine. Macrocyclic ring closure between the D-Phe and the L-Vty residues was performed via the pentafluorophenyl ester, and the Dess-Martin periodinane was used for the oxidation of the hydroxyamide to the alpha-ketoarginine (L-Kar) residue.

  DOI：

  10.1021/jo00073a010

文献信息

• Total synthesis of cyclotheonamide A
  作者：Peter Wipf、Hongyong Kim

  DOI：10.1021/jo00073a010

  日期：1993.10

  The potent serine protease inhibitor cyclotheonamide A was prepared in a convergent strategy from D-phenylalanine (D-Phe), vinylogous L-tyrosine (L-Vty), L-diaminopropanoic acid (L-Dpr), L-proline (L-Pro), and a hydroxy acid derivative of L-arginine. Macrocyclic ring closure between the D-Phe and the L-Vty residues was performed via the pentafluorophenyl ester, and the Dess-Martin periodinane was used for the oxidation of the hydroxyamide to the alpha-ketoarginine (L-Kar) residue.