ethyl N-(((benzyloxy)carbonyl)-L-tryptophyl)-S-ethynyl-L-cysteinate | 1452252-77-5

• 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: ethyl N-(((benzyloxy)carbonyl)-L-tryptophyl)-S-ethynyl-L-cysteinate
• CAS: 1452252-77-5
• 化学式: C₂₆H₂₇N₃O₅S
• 分子量: 493.583
• InChiKey: OSSQIKGXHCKMCX-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  109.52
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl N-(((benzyloxy)carbonyl)-L-tryptophyl)-S-ethynyl-L-cysteinate 、 N-(3-叠氮丙基)-5-(二甲氨基)萘-1-磺酰胺 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 氯仿 、 水 为溶剂， 反应 24.0h， 以93%的产率得到(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-((1-(3-(5-(dimethylamino)naphthalene-1-sulfonamido)propyl)-1H-1,2,3-triazol-4-yl)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-色氨酸 在 L-赖氨酸 、 四丁基氟化铵 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 L-组氨酸 、 四甲基胍 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 27.26h， 生成 ethyl N-(((benzyloxy)carbonyl)-L-tryptophyl)-S-ethynyl-L-cysteinate
  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