ditert-butyl 4-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]-4-[[(2S,3S,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxane-2-carbonyl]amino]heptanedioate | 724766-14-7

• 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,6S)-3,4,5,6-tetraacetyloxyoxane-2-carbonyl]amino]heptanedioate
• CAS: 724766-14-7
• 化学式: C₃₆H₅₇NO₁₆
• 分子量: 759.846
• InChiKey: RZCYXRFPVWNHNL-SIKAAIQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  53
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  222
• 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,6S)-3,4,5,6-tetraacetyloxyoxane-2-carbonyl]amino]heptanedioate 在 吡啶 、 二甲胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以1.51 g的产率得到ditert-butyl 4-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]-4-[[(2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-hydroxyoxane-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
• 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 、 1,2,3,4-tetra-O-acetyl-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53%的产率得到ditert-butyl 4-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]-4-[[(2S,3S,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxane-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