(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-3-mercaptopropanoate | 1443746-74-4

• 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: (R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-3-mercaptopropanoate
• CAS: 1443746-74-4
• 化学式: C₂₂H₂₆N₂O₆S
• 分子量: 446.524
• InChiKey: AVKUBHAUMRWUBV-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113.96
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-3-mercaptopropanoate 、 1-[(三异丙基硅烷基)乙炔基]-1,2-苯碘酰-3(1H)-酮 在 四甲基胍 作用下， 以 四氢呋喃 为溶剂， 反应 0.16h， 以96%的产率得到(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate
  参考文献：
  名称：

  A Highly Chemoselective and Practical Alkynylation of Thiols

  摘要：

  A thiol-alkynylation procedure utilizing the hypervalent iodine alkyne transfer reagent TIPS-ethynyl-benziodoxolone has been developed. This scalable reaction proceeds in five minutes at room temperature in an open flask using commercially available reagents. The scope of the reaction is broad, with a variety of phenolic, benzylic, heterocyclic, and aliphatic thiols undergoing alkynylation in excellent yield. The method is highly chemoselective as a vast array of functional groups are tolerated. The utility of the thiol-alkynylation in postsynthetic elaboration has been demonstrated through the facile installment of a fluorophore tag on a cysteine-containing peptide.

  DOI：

  10.1021/ja4044196
• 作为产物：
  描述：

  N-苄氧羰基-L-酪氨酸 、 L-半胱氨酸乙酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)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 14.17h， 以33%的产率得到(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanamido)-3-mercaptopropanoate
  参考文献：
  名称：

  A Highly Chemoselective and Practical Alkynylation of Thiols

  摘要：

  A thiol-alkynylation procedure utilizing the hypervalent iodine alkyne transfer reagent TIPS-ethynyl-benziodoxolone has been developed. This scalable reaction proceeds in five minutes at room temperature in an open flask using commercially available reagents. The scope of the reaction is broad, with a variety of phenolic, benzylic, heterocyclic, and aliphatic thiols undergoing alkynylation in excellent yield. The method is highly chemoselective as a vast array of functional groups are tolerated. The utility of the thiol-alkynylation in postsynthetic elaboration has been demonstrated through the facile installment of a fluorophore tag on a cysteine-containing peptide.

  DOI：

  10.1021/ja4044196