(2R,3S,4R,5S)-acetic acid 3,4-bis-allyloxy-5-(benzoylamino-naphthalen-1-yl-methyl)-6-ethoxy-tetrahydro-pyran-2-ylmethyl ester | 1332628-50-8

• 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: (2R,3S,4R,5S)-acetic acid 3,4-bis-allyloxy-5-(benzoylamino-naphthalen-1-yl-methyl)-6-ethoxy-tetrahydro-pyran-2-ylmethyl ester
• 英文别名: [(2R,3S,4R,5R,6R)-5-[(S)-benzamido(naphthalen-1-yl)methyl]-6-ethoxy-3,4-bis(prop-2-enoxy)oxan-2-yl]methyl acetate
• CAS: 1332628-50-8
• 化学式: C₃₄H₃₉NO₇
• 分子量: 573.686
• InChiKey: XXQOXRPDSYKXJB-WXJWJZPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,6-三-O-甲基-D-葡萄糖醛 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 (2R,3S,4R,5S)-acetic acid 3,4-bis-allyloxy-5-(benzoylamino-naphthalen-1-yl-methyl)-6-ethoxy-tetrahydro-pyran-2-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