(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanamido)-3-mercaptopropanoate | 1443746-75-5

• 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-hydroxypropanamido)-3-mercaptopropanoate
• 英文别名: ethyl (2R)-2-[[(2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]-3-sulfanylpropanoate
• CAS: 1443746-75-5
• 化学式: C₁₆H₂₂N₂O₆S
• 分子量: 370.426
• InChiKey: XMUVWJNCWFVMCJ-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanamido)-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98%的产率得到(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanamido)-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-丝氨酸 、 L-半胱氨酸乙酯盐酸盐 在 N-甲基吗啉 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以49%的产率得到(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanamido)-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

文献信息

• CN115108953
  申请人：——

  公开号：——

  公开（公告）日：——
• A Highly Chemoselective and Practical Alkynylation of Thiols
  作者：Reto Frei、Jérôme Waser

  DOI：10.1021/ja4044196

  日期：2013.7.3

  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.