tert-butyl (4S)-5-azido-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]pentanoate | 869735-65-9

• 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 (4S)-5-azido-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]pentanoate
• CAS: 869735-65-9
• 化学式: C₂₃H₃₅N₅O₅S₂
• 分子量: 525.693
• InChiKey: VSWYHRYOABIIBZ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-5-azido-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]pentanoate 、 alkaline earth salt of/the/ methylsulfuric acid 在 苯硫酚 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 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：

  (S)-4-Amino-5-azido-pentanoic acid tert-butyl ester 、 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl isothiocyanate 以 乙酸乙酯 为溶剂， 反应 2.0h， 以714 mg的产率得到tert-butyl (4S)-5-azido-4-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylcarbamothioylamino]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

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.