N-[(4,5-bis-allyloxy-6-allyloxymethyl-2-propoxy-tetrahydro-pyran-3-yl)-p-tolyl-methyl]-benzamide | 1332628-55-3

• 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: N-[(4,5-bis-allyloxy-6-allyloxymethyl-2-propoxy-tetrahydro-pyran-3-yl)-p-tolyl-methyl]-benzamide
• 英文别名: N-[(S)-[(2R,3R,4R,5R,6R)-4,5-bis(prop-2-enoxy)-6-(prop-2-enoxymethyl)-2-propoxyoxan-3-yl]-(4-methylphenyl)methyl]benzamide
• CAS: 1332628-55-3
• 化学式: C₃₃H₄₃NO₆
• 分子量: 549.708
• InChiKey: CSSRMZXLLISMAL-YLPVIMKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  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， 生成 N-[(4,5-bis-allyloxy-6-allyloxymethyl-2-propoxy-tetrahydro-pyran-3-yl)-p-tolyl-methyl]-benzamide
  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

文献信息

• Highly Facialselective Synthesis of Pyranose 1,3-Oxazines and Their Ring Opening with Nucleophiles: A Novel Entry to 2-<i>C</i>-Branched Glycosides
  作者：Biao-Lin Yin、Ze-Ren Zhang、Li-Wen Xu、Huanfeng Jiang

  DOI：10.1021/ol2019604

  日期：2011.10.7

  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.