N-(2-(tritylthio)ethyl)formamide

• 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: N-(2-(tritylthio)ethyl)formamide
• 英文别名: N-(2-tritylsulfanylethyl)formamide
• 化学式: C₂₂H₂₁NOS
• 分子量: 347.481
• InChiKey: KHFUDWHFIMBKSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-(tritylthio)ethyl)formamide 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 N1-methyl-N1-(4-methyl-1-oxo-1-((2-(tritylthio)ethyl)amino)pentan-2-yl)-N4-(2-(tritylthio) ethyl) succinamide
  参考文献：
  名称：

  Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics

  摘要：

  A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.

  DOI：

  10.1021/acs.orglett.7b01324
• 作为产物：
  描述：

  三苯基甲醇 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 生成 N-(2-(tritylthio)ethyl)formamide
  参考文献：
  名称：

  Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics

  摘要：

  A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.

  DOI：

  10.1021/acs.orglett.7b01324

文献信息

• A Peptide Backbone Stapling Strategy Enabled by the Multicomponent Incorporation of Amide N‐Substituents
  作者：Manuel G. Ricardo、Javiel F. Marrrero、Oscar Valdés、Daniel G. Rivera、Ludger A. Wessjohann

  DOI：10.1002/chem.201805318

  日期：2019.1.14

  N‐modification of peptides on solid‐phase is presented as a powerful and general method to enable peptide stapling at the backbone instead of the side chains. This work shows that a variety of functionalized N‐substituents suitable for backbone stapling can be readily introduced by means of on‐resin Ugi multicomponent reactions conducted during solid‐phase peptide synthesis. Diverse macrocyclization chemistries

  固相上肽的多组分主链N-修饰是一种强大而通用的方法，可在主链而不是侧链上进行肽钉接。这项工作表明，通过固相肽合成过程中进行的树脂上Ugi多组分反应可以很容易地引入各种适用于主链缝合的功能化N取代基。此类骨架N取代基可实现多种多样的大环化化学反应，包括闭环易位，内酰胺化和硫醇烷基化。通过将N-取代基连接到肽N-末端，骨架N-修饰方法也用于合成α-螺旋肽，从而具有氢键替代结构。全面的，
• US4203898A
  申请人：——

  公开号：US4203898A

  公开（公告）日：1980-05-20
• Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
  作者：Thimmalapura M. Vishwanatha、Enrico Bergamaschi、Alexander Dömling

  DOI：10.1021/acs.orglett.7b01324

  日期：2017.6.16

  A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.