4-(2-carboxyethyl)-4-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoylamino]oxane-2-carbonyl]amino]heptanedioic acid | 724766-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-(2-carboxyethyl)-4-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoylamino]oxane-2-carbonyl]amino]heptanedioic acid
• CAS: 724766-20-5
• 化学式: C₄₀H₄₇N₃O₁₇
• 分子量: 841.823
• InChiKey: MNAARDVFKIEGSI-WEQPGUHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  60
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  297
• 氢给体数：
  6
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2-aminoethyl α-D-mannopyranoside 、 4-(2-carboxyethyl)-4-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoylamino]oxane-2-carbonyl]amino]heptanedioic acid 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以50%的产率得到[(2S,3S,4S,5R,6R)-3,5-diacetyloxy-2-[[1,7-dioxo-4-[3-oxo-3-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylamino]propyl]-1,7-bis[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylamino]heptan-4-yl]carbamoyl]-6-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoylamino]oxan-4-yl] acetate
  参考文献：
  名称：

  Glucuronic Acid Derivatives as Branching Units for the Synthesis of Glycopeptide Mimetics

  摘要：

  Natural glycopeptides and glycoproteins exhibit a large structural diversity, which can be mimicked by synthetic glycopeptide derivatives to assist the investigation of biological functions and structure-activity relationships. Here, dendronized saccharides were synthesized to provide glycosyl amino acids, equipped with a branching element for the preparation of branched glycopeptide mimetics. An optimized Staudinger-type reaction served as key reaction en route to the complex glycopeptide 14, in which three mannose moieties were connected to the branched glucuronyl scaffold.

  DOI：

  10.1021/jo049708c
• 作为产物：
  描述：

  ditert-butyl 4-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]-4-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoylamino]oxane-2-carbonyl]amino]heptanedioate 在 三氟乙酸 作用下， 反应 1.0h， 以69%的产率得到4-(2-carboxyethyl)-4-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoylamino]oxane-2-carbonyl]amino]heptanedioic acid
  参考文献：
  名称：

  Glucuronic Acid Derivatives as Branching Units for the Synthesis of Glycopeptide Mimetics

  摘要：

  Natural glycopeptides and glycoproteins exhibit a large structural diversity, which can be mimicked by synthetic glycopeptide derivatives to assist the investigation of biological functions and structure-activity relationships. Here, dendronized saccharides were synthesized to provide glycosyl amino acids, equipped with a branching element for the preparation of branched glycopeptide mimetics. An optimized Staudinger-type reaction served as key reaction en route to the complex glycopeptide 14, in which three mannose moieties were connected to the branched glucuronyl scaffold.

  DOI：

  10.1021/jo049708c