1-[(2S)-1-azido-4-methylpentan-2-yl]-3-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]thiourea | 569371-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 1-[(2S)-1-azido-4-methylpentan-2-yl]-3-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]thiourea
• CAS: 569371-17-1
• 化学式: C₂₀H₃₁N₅O₃S₂
• 分子量: 453.63
• InChiKey: BAZWAPVRUCIDQU-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  、 1-[(2S)-1-azido-4-methylpentan-2-yl]-3-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]thiourea 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 4.0h， 生成
  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：

  Fmoc-Leu-N3 、 alkaline earth salt of/the/ methylsulfuric acid 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 2.33h， 生成 1-[(2S)-1-azido-4-methylpentan-2-yl]-3-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonyl]thiourea
  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

• Oligomeric guanidine synthesis assisted by TFA-sensitive arylsulfonylthiourea
  作者：Zhongsheng Zhang、Tyan Carter、Erkang Fan

  DOI：10.1016/s0040-4039(03)00543-4

  日期：2003.4

  Through arylsulfonyl activation of thiourea, efficient synthesis of oligomeric guanidines can be achieved in either solution or solid-phase. Incorporation of TFA-sensitive arylsulfonyl groups, such as Pbf, during the synthesis greatly simplifies deprotection procedures for obtaining the final oligomeric guanidine products. (C) 2003 Elsevier Science Ltd. All rights reserved.