methyl (2R,3S,6R)-6-(2-benzyloxyethyl)-2-(2-methyl-1,3-oxazol-4-yl)-4-oxotetrahydropyran-3-carboxylate | 1264193-74-9

• 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: methyl (2R,3S,6R)-6-(2-benzyloxyethyl)-2-(2-methyl-1,3-oxazol-4-yl)-4-oxotetrahydropyran-3-carboxylate
• 英文别名: methyl (2R,3S,6R)-2-(2-methyl-1,3-oxazol-4-yl)-4-oxo-6-(2-phenylmethoxyethyl)oxane-3-carboxylate
• CAS: 1264193-74-9
• 化学式: C₂₀H₂₃NO₆
• 分子量: 373.406
• InChiKey: IEHRREFFVYVCLN-LZQZEXGQSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  501.5±50.0 °C(predicted)
• 密度：
  1.207±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  87.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 6-(2-benzyloxyethyl)-4-hydroxy-2-(2-methyl-1,3-oxazol-4-yl)-5,6-dihydro-2H-pyran-3-carboxylate 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S,3R,6S)-6-(2-benzyloxyethyl)-2-(2-methyl-1,3oxazol-4-yl)-4-oxotetrahydropyran-3-carboxylate 、 methyl (2R,3S,6R)-6-(2-benzyloxyethyl)-2-(2-methyl-1,3-oxazol-4-yl)-4-oxotetrahydropyran-3-carboxylate
  参考文献：
  名称：

  The Asymmetric Maitland−Japp Reaction and Its Application to the Construction of the C1−C19 Bis-pyran Unit of Phorboxazole B

  摘要：

  The synthesis of the C1-C19 bis-pyran unit of phorboxazole B has been achieved. The key pyran rings were constructed by means of an asymmetric Maitland-Japp reaction and a second Maitland-Japp resolution/cyclization reaction. The longest linear sequence was 14 steps, and the C1-C19 bis-pyran unit was formed in an impressive 10.4% yield.

  DOI：

  10.1021/ol102860r

文献信息

• The Asymmetric Maitland−Japp Reaction and Its Application to the Construction of the C1−C19 <i>Bis</i>-pyran Unit of Phorboxazole B
  作者：Paul A. Clarke、Soraia Santos、Nimesh Mistry、Laurence Burroughs、Alexander C. Humphries

  DOI：10.1021/ol102860r

  日期：2011.2.18

  The synthesis of the C1-C19 bis-pyran unit of phorboxazole B has been achieved. The key pyran rings were constructed by means of an asymmetric Maitland-Japp reaction and a second Maitland-Japp resolution/cyclization reaction. The longest linear sequence was 14 steps, and the C1-C19 bis-pyran unit was formed in an impressive 10.4% yield.