(2R,3R,4S)-5-Fluoro-3,4-dimethoxy-2-methoxymethyl-3,4-dihydro-2H-pyran | 916453-13-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (2R,3R,4S)-5-Fluoro-3,4-dimethoxy-2-methoxymethyl-3,4-dihydro-2H-pyran
• 英文别名: (2R,3R,4S)-5-fluoro-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran
• CAS: 916453-13-9
• 化学式: C₉H₁₅FO₄
• 分子量: 206.214
• InChiKey: ZGPUVYGOPZRDKF-IWSPIJDZSA-N

物化性质

• 沸点：
  231.3±40.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-5-Fluoro-3,4-dimethoxy-2-methoxymethyl-3,4-dihydro-2H-pyran 在 三丁基氯化锡 、 叔丁基锂 、 碘 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R,4S)-5-Fluoro-6-iodo-3,4-dimethoxy-2-methoxymethyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  A synthesis of 2-fluoroglucal derivatives

  摘要：

  3,4,6-Tri-O-methyl-D-glucal, readily prepared from 3,4,6-tri-O-acetyl-D-glucal, undergoes lithiation at -78 degrees C in THF with t-BuLi to afford a vinyl carbanion, which can be trapped with electrophiles in moderate overall yields. The palladium coupling and Dotz-type reactions of these intermediates are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.122
• 作为产物：
  描述：

  (2R,3S,4S)-5-fluoro-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol 、 碘甲烷 在 sodium hydroxide 、 二甲基亚砜 作用下， 以69%的产率得到(2R,3R,4S)-5-Fluoro-3,4-dimethoxy-2-methoxymethyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  A synthesis of 2-fluoroglucal derivatives

  摘要：

  3,4,6-Tri-O-methyl-D-glucal, readily prepared from 3,4,6-tri-O-acetyl-D-glucal, undergoes lithiation at -78 degrees C in THF with t-BuLi to afford a vinyl carbanion, which can be trapped with electrophiles in moderate overall yields. The palladium coupling and Dotz-type reactions of these intermediates are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.122

文献信息

• A synthesis of 2-fluoroglucal derivatives
  作者：Ewan Boyd、Ray V.H. Jones、Peter Quayle、Anita J. Waring (née Potts)

  DOI：10.1016/j.tetlet.2006.08.122

  日期：2006.11

  3,4,6-Tri-O-methyl-D-glucal, readily prepared from 3,4,6-tri-O-acetyl-D-glucal, undergoes lithiation at -78 degrees C in THF with t-BuLi to afford a vinyl carbanion, which can be trapped with electrophiles in moderate overall yields. The palladium coupling and Dotz-type reactions of these intermediates are also described. (c) 2006 Elsevier Ltd. All rights reserved.