(4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-4-(3-nitro-phenyl)-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-6-yl ester | 1332628-31-5

• 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: (4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-4-(3-nitro-phenyl)-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-6-yl ester
• 英文别名: [(4S,4aS,6S,7R,8aR)-6-acetyloxy-4-(3-nitrophenyl)-2-phenyl-4,4a,5,6,7,8a-hexahydropyrano[3,2-e][1,3]oxazin-7-yl]methyl acetate
• CAS: 1332628-31-5
• 化学式: C₂₄H₂₄N₂O₈
• 分子量: 468.463
• InChiKey: PBXCGMAZORRGIL-XIFQGDJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-[methoxy-(3-nitro-phenyl)-methyl]-benzamide 、 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-1-enitol 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49%的产率得到(4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-4-(3-nitro-phenyl)-2-phenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-6-yl ester
  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