N-Cbz-D-phenylalanine p-toluene thioester | 1446350-31-7

• 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: N-Cbz-D-phenylalanine p-toluene thioester
• 英文别名: S-(4-methylphenyl) (2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanethioate
• CAS: 1446350-31-7
• 化学式: C₂₄H₂₃NO₃S
• 分子量: 405.518
• InChiKey: HFBRWORSKJYVLD-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甘氨酸乙酯盐酸盐 、 N-Cbz-D-phenylalanine p-toluene thioester 在 三乙胺 、 六甲基二硅氧烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以173 mg的产率得到Z-D-Phe-Gly-OEt
  参考文献：
  名称：

  HMDO-Promoted Peptide and Protein Synthesis in Ionic Liquids

  摘要：

  Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.

  DOI：

  10.1021/jo400797t
• 作为产物：
  描述：

  N-苄氧羰基-D-苯丙氨酸 、 4-甲苯硫酚 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以78%的产率得到N-Cbz-D-phenylalanine p-toluene thioester
  参考文献：
  名称：

  HMDO-Promoted Peptide and Protein Synthesis in Ionic Liquids

  摘要：

  Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.

  DOI：

  10.1021/jo400797t

文献信息

• HMDO-Promoted Peptide and Protein Synthesis in Ionic Liquids
  作者：Jianli Duan、Yao Sun、Hao Chen、Guofu Qiu、Haibing Zhou、Ting Tang、Zixin Deng、Xuechuan Hong

  DOI：10.1021/jo400797t

  日期：2013.7.19

  Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.