(2S)-4-[[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid | 511546-50-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-4-[[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
• CAS: 511546-50-2
• 化学式: C₃₇H₄₈N₂O₂₀
• 分子量: 840.79
• InChiKey: NRXXSLFBPALRJG-VIYKZHMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  59
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  353
• 氢给体数：
  13
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  1-羟基苯并三唑 、 (2S)-4-[[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 2.0h， 生成 benzotriazol-1-yl (2S)-4-[[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoate
  参考文献：
  名称：

  Efficient Synthesis of Complex Glycopeptides Based on Unprotected Oligosaccharides

  摘要：

  N-Glycopeptides containing 1 to 4 trisaccharide chains, with the carbohydrates vicinal to each other in the multivalent glycopeptides, were efficiently synthesized by using the glycosylated Fmoc-asparagine as a key building block. While the couplings of amino acids with glycopeptides could be achieved in the homogeneous solutions in N-methylpyrrolidinone (NMP) to give excellent yields, all products were conveniently isolated from the reaction mixtures through a precipitation method by using the free carbohydrate chains as phase tags. Commercially available pentafluorophenyl (Pfp) esters of amino acids were employed for the glycopeptide elongation. Longer glycopeptides were constructed by means of a highly convergent synthetic design that is based on the coupling of glycopeptide/peptide fragments. Hydrogen bond interactions between free oligosaccharides were proposed to explain the exceptionally high efficiency of the couplings between two glycosylated building blocks.

  DOI：

  10.1021/jo020570c
• 作为产物：
  描述：

  maltotriose 在 碳酸氢铵 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、1.72 MPa 条件下， 反应 29.5h， 生成 (2S)-4-[[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
  参考文献：
  名称：

  一种有效的合成途径，可用于糖肽合成的糖氨基酸结构单元。

  摘要：

  [反应：见正文]化学糖肽合成需要获得克量的糖基化氨基酸构件。因此，这种结构单元的合成效率非常重要。在这里，我们报告了一种快速高效的合成路线，可分三步以高收率从未保护的糖中合成Fmoc保护的天冬酰胺基糖苷。通过标准的Fmoc固相肽合成，将糖基化的氨基酸成功地掺入靶糖肽7和8中。

  DOI：

  10.1021/ol048342n

文献信息

• An Efficient Synthetic Route to Glycoamino Acid Building Blocks for Glycopeptide Synthesis
  作者：Mallesham Bejugam、Sabine L. Flitsch

  DOI：10.1021/ol048342n

  日期：2004.10.1

  requires access to gram quantities of glycosylated amino acid building blocks. Hence, the efficiency of synthesis of such building blocks is of great importance. Here, we report a fast and highly efficient synthetic route to Fmoc-protected asparaginyl glycosides from unprotected sugars in three steps with high yields. The glycosylated amino acids were successfully incorporated into target glycopeptides

  [反应：见正文]化学糖肽合成需要获得克量的糖基化氨基酸构件。因此，这种结构单元的合成效率非常重要。在这里，我们报告了一种快速高效的合成路线，可分三步以高收率从未保护的糖中合成Fmoc保护的天冬酰胺基糖苷。通过标准的Fmoc固相肽合成，将糖基化的氨基酸成功地掺入靶糖肽7和8中。
• Efficient Synthesis of Complex Glycopeptides Based on Unprotected Oligosaccharides
  作者：Jie Xue、Zhongwu Guo

  DOI：10.1021/jo020570c

  日期：2003.4.1

  N-Glycopeptides containing 1 to 4 trisaccharide chains, with the carbohydrates vicinal to each other in the multivalent glycopeptides, were efficiently synthesized by using the glycosylated Fmoc-asparagine as a key building block. While the couplings of amino acids with glycopeptides could be achieved in the homogeneous solutions in N-methylpyrrolidinone (NMP) to give excellent yields, all products were conveniently isolated from the reaction mixtures through a precipitation method by using the free carbohydrate chains as phase tags. Commercially available pentafluorophenyl (Pfp) esters of amino acids were employed for the glycopeptide elongation. Longer glycopeptides were constructed by means of a highly convergent synthetic design that is based on the coupling of glycopeptide/peptide fragments. Hydrogen bond interactions between free oligosaccharides were proposed to explain the exceptionally high efficiency of the couplings between two glycosylated building blocks.