tert-butyl (2S,2'S,2''R,1'''S,2''''S)-2-[2-(2-{1-[3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionylamino]-2-methylpropyl}-5-oxopyrrolidin-1-yl)-4-methylpentanoylamino]-3-phenylpropanoate | 1242316-81-9

• 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: tert-butyl (2S,2'S,2''R,1'''S,2''''S)-2-[2-(2-{1-[3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionylamino]-2-methylpropyl}-5-oxopyrrolidin-1-yl)-4-methylpentanoylamino]-3-phenylpropanoate
• 英文别名: tert-butyl (2S)-2-[[(2S)-2-[(2R)-2-[(1S)-1-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]propanoyl]amino]-2-methylpropyl]-5-oxopyrrolidin-1-yl]-4-methylpentanoyl]amino]-3-phenylpropanoate
• CAS: 1242316-81-9
• 化学式: C₄₉H₆₆N₄O₈
• 分子量: 839.085
• InChiKey: XGFJRXSHDBLXOO-VGZFNSLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  61
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,2'S,2''R)-2-{2-[2-(1-amino-2-methylpropyl)-5-oxopyrrolidin-1-yl]-4-methylpentanoylamido}-3-phenylpropanoate 、 FMOC-O-叔丁基-L-丝氨酸 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57%的产率得到tert-butyl (2S,2'S,2''R,1'''S,2''''S)-2-[2-(2-{1-[3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionylamino]-2-methylpropyl}-5-oxopyrrolidin-1-yl)-4-methylpentanoylamino]-3-phenylpropanoate
  参考文献：
  名称：

  γ-Lactam-containing peptidomimetics

  摘要：

  Protected diaminoalcohols obtained through allyl addition to alpha-amino acid-derived imines and subsequent hydroboration were used for the preparation of pyrrolidinones and pyrrolidines. Pyrrolidinones were synthesized with moderate yields by oxidation of the hydroxy function with tetrapropylammonium perruthenate/N-methylmorpholine-N-oxide and concomitant cyclization while pyrrolidines were synthesized in good yields by tosylation of the hydroxy group and subsequent intramolecular nucleophilic substitution. Thus accessible substrates were transferred into peptidomimetics by attachment of amino acid moieties at both termini using conventional peptide coupling strategies. Molecular mechanics optimizations suggest that these substrates preferentially adopt a turn conformation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.099

文献信息

• γ-Lactam-containing peptidomimetics
  作者：Mickael Virlouvet、Joachim Podlech

  DOI：10.1016/j.tet.2010.05.099

  日期：2010.8

  Protected diaminoalcohols obtained through allyl addition to alpha-amino acid-derived imines and subsequent hydroboration were used for the preparation of pyrrolidinones and pyrrolidines. Pyrrolidinones were synthesized with moderate yields by oxidation of the hydroxy function with tetrapropylammonium perruthenate/N-methylmorpholine-N-oxide and concomitant cyclization while pyrrolidines were synthesized in good yields by tosylation of the hydroxy group and subsequent intramolecular nucleophilic substitution. Thus accessible substrates were transferred into peptidomimetics by attachment of amino acid moieties at both termini using conventional peptide coupling strategies. Molecular mechanics optimizations suggest that these substrates preferentially adopt a turn conformation. (C) 2010 Elsevier Ltd. All rights reserved.