N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanyl-L-serine benzyl ester | 1174725-55-3

• 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]-L-phenylalanyl-L-serine benzyl ester
• 英文别名: N-(9-fluorenylmethoxycarbonyl)-L-phenylalanine-L-serine benzyl ester；Fmoc-L-Phe-L-Ser-OBn；Fmoc-Phe-Ser-OBn；benzyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]-3-hydroxypropanoate
• CAS: 1174725-55-3
• 化学式: C₃₄H₃₂N₂O₆
• 分子量: 564.638
• InChiKey: KVWSZFYGBJXMDN-CONSDPRKSA-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]-L-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78%的产率得到环(L-苯丙氨酰-L-丝氨酰)
  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：

  N-(9-fluorenylmethoxycarbonyl)-L-phenylalanine-O-(triethylsilyl)-L-serine benzyl ester 在 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以63%的产率得到N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanyl-L-serine benzyl ester
  参考文献：
  名称：

  Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon–Oxygen Bonds

  摘要：

  This Article describes the development of conditions for cleaving silicon oxygen bonds using catalytic quantities of fluoride at neutral pH in mixed organic aqueous solutions that contain buffer. A variety of silicon protecting groups can be removed under these conditions, which show tolerance for acid- and base-sensitive groups. A modified procedure also is presented using catalytic fluoride in anhydrous dimethyl sulfoxide-methanol, which generates primarily volatile silicon byproducts.

  DOI：

  10.1021/jo200848j

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.
• Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon–Oxygen Bonds
  作者：Anthony M. DiLauro、Wanji Seo、Scott T. Phillips

  DOI：10.1021/jo200848j

  日期：2011.9.16

  This Article describes the development of conditions for cleaving silicon oxygen bonds using catalytic quantities of fluoride at neutral pH in mixed organic aqueous solutions that contain buffer. A variety of silicon protecting groups can be removed under these conditions, which show tolerance for acid- and base-sensitive groups. A modified procedure also is presented using catalytic fluoride in anhydrous dimethyl sulfoxide-methanol, which generates primarily volatile silicon byproducts.