tert-butyl (S)-2-((tert-butoxycarbonyl)amino)-5-<2,2-(1,3-dithiolanyl)>-5-(4-methoxyphenyl)pentanoate | 174464-32-5

• 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: tert-butyl (S)-2-((tert-butoxycarbonyl)amino)-5-<2,2-(1,3-dithiolanyl)>-5-(4-methoxyphenyl)pentanoate
• 英文别名: tert-butyl (2S)-4-[2-(4-methoxyphenyl)-1,3-dithiolan-2-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 174464-32-5
• 化学式: C₂₃H₃₅NO₅S₂
• 分子量: 469.667
• InChiKey: JAMNWDGNLKHDRK-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-((tert-butoxycarbonyl)amino)-5-<2,2-(1,3-dithiolanyl)>-5-(4-methoxyphenyl)pentanoate 在 N-甲基吗啉 、 N-甲基咪唑 、 盐酸 、 mercury(II) perchlorate 、 1,1'-carbonylbis(3-methylimidazolium) triflate 、 三乙胺 、 N,N'-羰基二咪唑 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 45.72h， 生成 BOC-Met-An^pGlu-Ile-OCH3
  参考文献：
  名称：

  Synthesis of Anisolylated Aspartyl and Glutamyl Tripeptides

  摘要：

  A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation-the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.

  DOI：

  10.1021/jo951754c
• 作为产物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-5-(4-methoxy-phenyl)-5-oxo-pentanoic acid tert-butyl ester 在 三氟甲磺酸 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 tert-butyl (S)-2-((tert-butoxycarbonyl)amino)-5-<2,2-(1,3-dithiolanyl)>-5-(4-methoxyphenyl)pentanoate
  参考文献：
  名称：

  Synthesis of Anisolylated Aspartyl and Glutamyl Tripeptides

  摘要：

  A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation-the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.

  DOI：

  10.1021/jo951754c

文献信息

• Synthesis of Anisolylated Aspartyl and Glutamyl Tripeptides
  作者：Fabienne Berrée、Kieyoung Chang、Agustín Cobas、Henry Rapoport

  DOI：10.1021/jo951754c

  日期：1996.1.1

  A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation-the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.