[(S)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(trityl-carbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester | 869735-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(S)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(trityl-carbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2S)-1-(1,3-dioxoisoindol-2-yl)-4-oxo-4-(tritylamino)butan-2-yl]carbamate
• CAS: 869735-96-6
• 化学式: C₄₆H₃₇N₃O₅
• 分子量: 711.817
• InChiKey: IQQUQVJPXRRWBY-UMSFTDKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(S)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(trityl-carbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙酸乙酯 为溶剂， 反应 0.17h， 生成 (S)-3-Amino-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-trityl-butyramide
  参考文献：
  名称：

  Solid-Phase and Solution-Phase Syntheses of Oligomeric Guanidines Bearing Peptide Side Chains

  摘要：

  Synthetic strategies for preparing N,N'-bridged oligomeric guanidines bearing peptide side chains both on solid support and in solution are presented. Monomers are prepared from common a-amino acids and therefore contain conventionally protected peptide side chains. The side chains include alkyl, aromatic, hydroxyl, amino, carboxylic acid, and amide functional groups. Oligomer elongation utilizes acid-sensitive sulfonyl activated thiourea through the formation of carbodiimide intermediate. With proper preparation of monomers, synthesis of oligomer can be performed in two directions (equivalent to N to C terminal or C to N terminal in a peptide sequence) with excellent efficiency.

  DOI：

  10.1021/jo051226t
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 N-Triphenylmethyl (3S)-3-(9-fluorenylmethoxycarbonylamino)-4-hydroxybutyramide 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到[(S)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(trityl-carbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Solid-Phase and Solution-Phase Syntheses of Oligomeric Guanidines Bearing Peptide Side Chains

  摘要：

  Synthetic strategies for preparing N,N'-bridged oligomeric guanidines bearing peptide side chains both on solid support and in solution are presented. Monomers are prepared from common a-amino acids and therefore contain conventionally protected peptide side chains. The side chains include alkyl, aromatic, hydroxyl, amino, carboxylic acid, and amide functional groups. Oligomer elongation utilizes acid-sensitive sulfonyl activated thiourea through the formation of carbodiimide intermediate. With proper preparation of monomers, synthesis of oligomer can be performed in two directions (equivalent to N to C terminal or C to N terminal in a peptide sequence) with excellent efficiency.

  DOI：

  10.1021/jo051226t

文献信息

• Solid-Phase and Solution-Phase Syntheses of Oligomeric Guanidines Bearing Peptide Side Chains
  作者：Zhongsheng Zhang、Erkang Fan

  DOI：10.1021/jo051226t

  日期：2005.10.1

  Synthetic strategies for preparing N,N'-bridged oligomeric guanidines bearing peptide side chains both on solid support and in solution are presented. Monomers are prepared from common a-amino acids and therefore contain conventionally protected peptide side chains. The side chains include alkyl, aromatic, hydroxyl, amino, carboxylic acid, and amide functional groups. Oligomer elongation utilizes acid-sensitive sulfonyl activated thiourea through the formation of carbodiimide intermediate. With proper preparation of monomers, synthesis of oligomer can be performed in two directions (equivalent to N to C terminal or C to N terminal in a peptide sequence) with excellent efficiency.