(4S,5R,6R,7S,4aS,8aR)-5,6-bis-allyloxy-7-allyloxymethyl-4-(4-bromo-phenyl)-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazine | 1332628-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R,6R,7S,4aS,8aR)-5,6-bis-allyloxy-7-allyloxymethyl-4-(4-bromo-phenyl)-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazine
• CAS: 1332628-45-1
• 化学式: C₂₉H₃₂BrNO₅
• 分子量: 554.481
• InChiKey: NXDKTACGRJXNIV-CQQPOQSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  58.51
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-benzoyl-1-methoxy-1-(p-bromophenyl)-methylamine 、 tri-O-allyl-D-lyxo-hexapyranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到(4S,5R,6R,7S,4aS,8aR)-5,6-bis-allyloxy-7-allyloxymethyl-4-(4-bromo-phenyl)-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazine
  参考文献：
  名称：

  Highly Facialselective Synthesis of Pyranose 1,3-Oxazines and Their Ring Opening with Nucleophiles: A Novel Entry to 2-C-Branched Glycosides

  摘要：

  A TMSOTf-promoted cycloaddition of N-benzoyl-N,O-acetals with various glycals and 3-deoxy glycals affords pyranose 1,3-oxazines with high facial selectivity. In addition, a highly diastereoselective ring opening of the resulting pyranose 1,3-oxazines is reported. With diverse nucleophiles, these reactions take place upon heating at 80 degrees C. This novel ring-opening reaction affords structurally diversified 2-C-branched glycosides with three newly formed contiguous stereocenters.

  DOI：

  10.1021/ol2019604