methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[[2-(4-nitrophenyl)sulfanyl-2-oxoethyl]amino]-4-oxobutanoate | 928342-39-6

• 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: methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[[2-(4-nitrophenyl)sulfanyl-2-oxoethyl]amino]-4-oxobutanoate
• CAS: 928342-39-6
• 化学式: C₁₈H₂₃N₃O₈S
• 分子量: 441.462
• InChiKey: VUYSEJSWDHAXIR-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 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：
  182
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[[2-(4-nitrophenyl)sulfanyl-2-oxoethyl]amino]-4-oxobutanoate 在 N,N-二异丙基乙胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 silver(I) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 Boc-Asp(OMe)-Gly-Gly-Thr(Bn)-Gly-Thr(Bn)-Lys(Cbz)-OMe
  参考文献：
  名称：

  Facile peptide thioester synthesis via solution-phase tosylamide preparation

  摘要：

  Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.143
• 作为产物：
  描述：

  2-[[(2S)-4-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]acetic acid 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[[2-(4-nitrophenyl)sulfanyl-2-oxoethyl]amino]-4-oxobutanoate
  参考文献：
  名称：

  Facile peptide thioester synthesis via solution-phase tosylamide preparation

  摘要：

  Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.143

文献信息

• Facile peptide thioester synthesis via solution-phase tosylamide preparation
  作者：Shino Manabe、Tomoyuki Sugioka、Yukishige Ito

  DOI：10.1016/j.tetlet.2006.11.143

  日期：2007.1

  Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation. (c) 2006 Elsevier Ltd. All rights reserved.