(6S,9R,12R)-12-(mercaptomethyl)-2,2,6-trimethyl-4,7,10-trioxo-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-triazatridecan-13-oic acid | 1430084-11-9

• 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: (6S,9R,12R)-12-(mercaptomethyl)-2,2,6-trimethyl-4,7,10-trioxo-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-triazatridecan-13-oic acid
• 英文别名: (2R)-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]-3-sulfanylpropanoic acid
• CAS: 1430084-11-9
• 化学式: C₃₁H₄₉N₃O₁₆S₂
• 分子量: 783.873
• InChiKey: FCHMWAXOWATLEM-SVXBGRRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  52
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  284
• 氢给体数：
  5
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (6S,9R,12R)-12-(mercaptomethyl)-2,2,6-trimethyl-4,7,10-trioxo-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-triazatridecan-13-oic acid 在 N-甲基吗啉 、 三丁基膦 、 安息香双甲醚 、 对甲氧基苯乙酮 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-[[(6S,9R)-2,2,6-trimethyl-4,7-dioxo-9-[[(S)-1-oxo-1-(phenylthio)propan-2-yl]-carbamoyl]-3-oxa-11-thia-5,8-diazatetradecan-14-yl]oxy]-tetrahydro-2H-pyran-3,4,5-triyl triacetate
  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
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 在 N-甲基吗啉 、 sodium tetrahydroborate 、 安息香双甲醚 、 对甲氧基苯乙酮 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 (6S,9R,12R)-12-(mercaptomethyl)-2,2,6-trimethyl-4,7,10-trioxo-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-triazatridecan-13-oic 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