(3R,4R,5R,6S,7R)-4,5,6-tris(benzyloxy)-7-ethylazepan-3-ol | 1354826-58-6

• 英文名称: (3R,4R,5R,6S,7R)-4,5,6-tris(benzyloxy)-7-ethylazepan-3-ol
• 英文别名: (3R,4R,5R,6S,7R)-7-ethyl-4,5,6-tris(phenylmethoxy)azepan-3-ol
• CAS: 1354826-58-6
• 化学式: C₂₉H₃₅NO₄
• 分子量: 461.601
• InChiKey: KVTBUGYZGFMVBJ-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose 在 solid supported triphenylphosphine 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (3R,4R,5R,6S,7R)-4,5,6-tris(benzyloxy)-7-ethylazepan-3-ol
  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