(S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid tert-butyl ester | 869735-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-5-(1,3-dioxoisoindol-2-yl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoate
• CAS: 869735-94-4
• 化学式: C₃₂H₃₂N₂O₆
• 分子量: 540.616
• InChiKey: SQNBKCFAXOWTNC-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid tert-butyl ester 在 triflic azide 、 一水合肼 、 copper(II) sulfate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 13.17h， 生成 (S)-4-Azido-5-({(2,4-dimethoxy-benzylamino)-[(E)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl}-amino)-pentanoic acid tert-butyl 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
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 (4S)-4-{[(9H-芴-9-基甲氧基)羰基]氨基}-5-羟基戊酸叔丁酯 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89%的产率得到(S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid tert-butyl 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.