N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanyl-L-serine benzyl ester | 1174725-57-5

• 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: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanyl-L-serine benzyl ester
• 英文别名: Fmoc-D-Phe-L-Ser-OBn；Fmoc-D-Phe-Ser-OBn；benzyl (2S)-2-[[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]-3-hydroxypropanoate
• CAS: 1174725-57-5
• 化学式: C₃₄H₃₂N₂O₆
• 分子量: 564.638
• InChiKey: KVWSZFYGBJXMDN-JSOSNVBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanyl-L-serine benzyl ester 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 以70%的产率得到cyclo(D-Phe-L-Ser)
  参考文献：
  名称：

  Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

  摘要：

  This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.069
• 作为产物：
  描述：

  丝氨酸苄酯盐酸盐 、 Fmoc-D-苯丙氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以85%的产率得到N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanyl-L-serine benzyl ester
  参考文献：
  名称：

  Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

  摘要：

  This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.069

文献信息

• Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs
  作者：Vanessa L. Campo、Maristela B. Martins、Carlos H.T.P. da Silva、Ivone Carvalho

  DOI：10.1016/j.tet.2009.04.069

  日期：2009.7

  This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.