(2S,3S,4R,5R,6S)-tert-butyl 6-(4-nitrobenzoyloxy)-2-allyl-3,4,5-tris(benzyloxy)azepane-1-carboxylate | 1354826-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4R,5R,6S)-tert-butyl 6-(4-nitrobenzoyloxy)-2-allyl-3,4,5-tris(benzyloxy)azepane-1-carboxylate
• CAS: 1354826-78-0
• 化学式: C₄₂H₄₆N₂O₉
• 分子量: 722.835
• InChiKey: HKELIYUZOJBLSR-NREVGYPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.07
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  126.67
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6S)-tert-butyl 6-(4-nitrobenzoyloxy)-2-allyl-3,4,5-tris(benzyloxy)azepane-1-carboxylate 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以93%的产率得到(2S,3S,4R,5R,6S)-tert-butyl 2-allyl-3,4,5-tris(benzyloxy)-6-hydroxyazepane-1-carboxylate
  参考文献：
  名称：

  Access to l- and d-Iminosugar C-Glycosides from a d-gluco-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy

  摘要：

  A flexible synthetic access to six-membered and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.

  DOI：

  10.1021/ol203385w
• 作为产物：
  描述：

  6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose 在 potassium hydrogencarbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 8.0h， 生成 (2S,3S,4R,5R,6S)-tert-butyl 6-(4-nitrobenzoyloxy)-2-allyl-3,4,5-tris(benzyloxy)azepane-1-carboxylate
  参考文献：
  名称：

  Access to l- and d-Iminosugar C-Glycosides from a d-gluco-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy

  摘要：

  A flexible synthetic access to six-membered and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.

  DOI：

  10.1021/ol203385w