(2R)-3-[5-[4-[3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)amino]-3-oxopropyl]triazol-1-yl]pentylsulfanyl]-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-[3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropylsulfanyl]propanoyl]amino]propanoyl]amino]propanoic acid | 1430084-23-3

• 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: (2R)-3-[5-[4-[3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)amino]-3-oxopropyl]triazol-1-yl]pentylsulfanyl]-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-[3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropylsulfanyl]propanoyl]amino]propanoyl]amino]propanoic acid
• CAS: 1430084-23-3
• 化学式: C₆₄H₈₀N₈O₂₃S₂
• 分子量: 1393.51
• InChiKey: ISSOYGCHQRRHOK-ISCXQZKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  97
• 可旋转键数：
  38
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  473
• 氢给体数：
  8
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  (6S,9R,12S,15R)-15-[[(5-azidopentyl)thio]methyl]-2,2,6,12-tetramethyl-4,7,10,13-tetraoxo-9-[[[3-[[(2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl]oxy]-propyl]thio]methyl]-3-oxa-5,8,11,14-tetraazahexadecan-16-oic acid 、 N-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)pent-4-ynamide 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 sodium ascorbate 、 三(3-羟丙基三唑甲基)胺 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 以65%的产率得到(2R)-3-[5-[4-[3-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)amino]-3-oxopropyl]triazol-1-yl]pentylsulfanyl]-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-[3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropylsulfanyl]propanoyl]amino]propanoyl]amino]propanoic acid
  参考文献：
  名称：

  Native Chemical Ligation,Thiol–Ene Click: A Methodology for the Synthesis of Functionalized Peptides

  摘要：

  The sequential combination of native chemical ligation and thiol-ene radical chemistry (NCL-TEC) on the resulting cysteine thiol has been investigated as a methodology for rapidly accessing functionalized peptides. Three sequential cycles of native chemical ligation and subsequent thiyl radical reactions (including a free-radical-mediated desulfurization reaction) were carried out on a peptide backbone demonstrating the iterative nature of this process. The versatility of the thiyl radical reaction at cysteine was demonstrated through the introduction of a number of different side chains including an amino acid derivative, a carbohydrate group, and an alkyl azide. Conditions were developed that allowed the sequential NCL-TEC process to proceed in high yield.

  DOI：

  10.1021/jo4001542