tert-butyl N-(5-nitro-1H-benzimidazol-2-yl)-S-trityl-L-cysteinate | 1431526-37-2

• 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: tert-butyl N-(5-nitro-1H-benzimidazol-2-yl)-S-trityl-L-cysteinate
• 英文别名: tert-butyl (2R)-2-[(6-nitro-1H-benzimidazol-2-yl)amino]-3-tritylsulfanylpropanoate
• CAS: 1431526-37-2
• 化学式: C₃₃H₃₂N₄O₄S
• 分子量: 580.707
• InChiKey: VRCCCKYGIWLGAR-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  H-半胱氨酸(TRT)-OTBU 在 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.92h， 生成 tert-butyl N-(5-nitro-1H-benzimidazol-2-yl)-S-trityl-L-cysteinate 、 tert-butyl 2-{(2Z)-2-[(2-amino-4-nitrophenyl)imino]-4-oxo-1,3-thiazolidin-3-yl}-3-(tritylsulfanyl)propanoate
  参考文献：
  名称：

  Iodoacetic Acid is an Efficient Reagent for the Synthesis of Amino Acid Derived 2-Aminobenzimidazoles

  摘要：

  Chiral, nonracemic, N-unprotected amino acids were converted into the corresponding N-benzimidazol-2-yl derivatives by a sequential procedure involving initial formation of isothiocyanates, their reaction with arene-1,2-diamines, and cyclization-desulfurization of the intermediate thioureas with iodoacetic acid. The simplified workup and the lack of volatile or toxic byproducts in the key desulfurization step renders iodoacetic acid a superior reagent to the usual reagent, iodomethane.

  DOI：

  10.1055/s-0032-1316849

文献信息

• Iodoacetic Acid is an Efficient Reagent for the Synthesis of Amino Acid Derived 2-Aminobenzimidazoles
  作者：Edgars Suna、Andrejs Krasikovs、Vita Ozola、Scott Dax

  DOI：10.1055/s-0032-1316849

  日期：——

  Chiral, nonracemic, N-unprotected amino acids were converted into the corresponding N-benzimidazol-2-yl derivatives by a sequential procedure involving initial formation of isothiocyanates, their reaction with arene-1,2-diamines, and cyclization-desulfurization of the intermediate thioureas with iodoacetic acid. The simplified workup and the lack of volatile or toxic byproducts in the key desulfurization step renders iodoacetic acid a superior reagent to the usual reagent, iodomethane.