(2S,3R,4S,5S,6R)-2-(4-((E)-2-fluoro-2-(4,4,6-trimethyl-5,6-dihydro-4H-1,3-oxazin-2-yl)vinyl)-2-methoxyphenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 1427072-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S,6R)-2-(4-((E)-2-fluoro-2-(4,4,6-trimethyl-5,6-dihydro-4H-1,3-oxazin-2-yl)vinyl)-2-methoxyphenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS: 1427072-23-8
• 化学式: C₂₂H₃₀FNO₈
• 分子量: 455.481
• InChiKey: BNUPOMUOWDABKJ-GQOPKPSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  130.2
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 、 [Fluoro-(4,4,6-trimethyl-5,6-dihydro-1,3-oxazin-2-yl)methyl]-triphenylphosphanium;bromide 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 以10%的产率得到
  参考文献：
  名称：

  A new approach to the synthesis of (Z)-2-fluoro-2-alkenals via Wittig-type carbonyl condensation reactions of 2-(fluoromethyl)-4,4,6-trimethyl-1,3-oxazine phosphonium bromide

  摘要：

  We report here the transformation of aldehydes to their (Z)-alpha-fluoro-alpha,beta-unsaturated aldehyde homologs by condensation with the phosphonium salt of the Meyer's oxazine obtained from bromofluoroacetonitrile. After methylation with trimethyloxonium tetrafluoroborate the quaternized oxazine is cleanly reduced to mostly Z 2-fluoro-2-alkenals by sodium borohydride at room temperature. This methodology is compatible with usual protecting groups and affords an efficient access to functionalized mostly Z 2-fluoro-2-alkenals derived from natural products and their corresponding (Z)-2-fluoro-2-alkenols. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.017