(3S)-3-azido-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]-N-tritylbutanamide | 869736-06-1

• 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: (3S)-3-azido-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]-N-tritylbutanamide
• CAS: 869736-06-1
• 化学式: C₃₇H₄₀N₆O₄S₂
• 分子量: 696.894
• InChiKey: GEMXZIBAVDDHRR-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S)-3-azido-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]-N-tritylbutanamide 、 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以387 mg的产率得到tert-butyl (4S)-4-[[(E)-N-[(2S)-2-[[(E)-N-[(2S)-2-[[(E)-N-[(2S)-2-[[(Z)-N-[[(2S)-1-[(E)-N-[(2S)-2-azido-4-oxo-4-(tritylamino)butyl]-N'-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]carbamimidoyl]pyrrolidin-2-yl]methyl]-N'-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]carbamimidoyl]amino]-4-methylpentyl]-N'-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]carbamimidoyl]amino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propyl]-N'-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]carbamimidoyl]amino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]-N'-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]carbamimidoyl]amino]-5-[[(E)-N-[(2,4-dimethoxyphenyl)methyl]-N'-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]carbamimidoyl]amino]pentanoate
  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：

  N-Triphenylmethyl (3S)-3-(9-fluorenylmethoxycarbonylamino)-4-hydroxybutyramide 在 triflic azide 、 一水合肼 、 copper(II) sulfate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 9.17h， 生成 (3S)-3-azido-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]-N-tritylbutanamide
  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.