1,3,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranose | 1427042-93-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6R)-4,6-diacetyloxy-5-fluoro-3-hydroxyoxan-2-yl]methyl acetate
• CAS: 1427042-93-0
• 化学式: C₁₂H₁₇FO₈
• 分子量: 308.261
• InChiKey: UXDVSKLGLMSXGQ-OOCWMUITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S,5R)-4,6-diacetyloxy-5-fluoro-3-phenylmethoxyoxan-2-yl]methyl acetate 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 1,3,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranose 、 1,3,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of a Dual-Purpose 2-Deoxy-2-fluoro-glucopyranosyl Building Block

  摘要：

  We demonstrate a straightforward route to 1,3,6-tri-O-acetyl-4-O-benzyl-2-deoxy-2-fluoro-D-glucopyranose through potassium hydrogen fluoride opening of a erny epoxide under microwave irradiation followed by acetolysis. The fluoroglucose building block was used as a key intermediate in the synthesis of 2,2-dideoxy-2,2-difluoromaltose. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.648001