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 | 724766-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 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
• CAS: 724766-18-1
• 化学式: C₅₂H₇₁N₃O₁₇
• 分子量: 1010.15
• InChiKey: SZINBCWDRIYFBU-OQDWTXKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  72
• 可旋转键数：
  30
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  264
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid 在 1-羟基苯并三唑 、 达卡巴嗪 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 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
  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