(4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-6-yl ester | 1332628-26-8

• 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: (4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-6-yl ester
• CAS: 1332628-26-8
• 化学式: C₂₄H₂₅NO₆
• 分子量: 423.466
• InChiKey: JHHJOVLKJNNHSR-XIFQGDJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.42
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  乙醇 、 (4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-2,4-diphenyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano[3,2-e][1,3]oxazin-6-yl ester 以88%的产率得到(2'S,2R,3S,5S)-acetic acid 2-acetoxymethyl-5-(benzoylamino-phenylmethyl)-6-ethoxy-tetrahydro-pyran-3-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
• 作为产物：
  描述：

  N-(1-ethoxy-1-phenylmethyl)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， 生成 (4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-2,4-diphenyl-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