3,4-di-O-(2-propenyl)-6-O-acetyl-D-glucal | 1332628-80-4

• 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: 3,4-di-O-(2-propenyl)-6-O-acetyl-D-glucal
• CAS: 1332628-80-4
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: DJMYDUBYGRYDCM-MCIONIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-benzoyl-1-methoxy-1-(p-methylphenyl)-methylamine 、 3,4-di-O-(2-propenyl)-6-O-acetyl-D-glucal 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,5R,6S,8aR)-acetic acid 5,6-bis-allyloxy-2-phenyl-4-p-tolyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano [3,2-e][1,3]oxazin-7-ylmethyl ester 、 acetic acid 5,6-bis-allyloxy-2-phenyl-4-p-tolyl-4a,6,7,8a-tetrahydro-4H,5H-pyrano [3,2-e][1,3]oxazin-7-ylmethyl 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