ditert-butyl 4-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]-4-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-azidooxane-2-carbonyl]amino]heptanedioate | 724766-17-0

• 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: ditert-butyl 4-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]-4-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-azidooxane-2-carbonyl]amino]heptanedioate
• CAS: 724766-17-0
• 化学式: C₃₄H₅₄N₄O₁₄
• 分子量: 742.821
• InChiKey: DQHCNKUIJSQAQD-RKBVRRORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  52
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  211
• 氢给体数：
  1
• 氢受体数：
  16

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-azidooxane-2-carbonyl]amino]heptanedioate 在 1-羟基苯并三唑 、 达卡巴嗪 、 三氟乙酸 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 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：

  4-[2-(叔丁氧羰基)乙基]-4-氨基戊烷二甲酸二叔丁酯 、 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 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到ditert-butyl 4-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]-4-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-azidooxane-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