(3aS,4S,6R,7S,7aR)-7-fluoro-6-(fluoromethyl)-4-methoxytetrahydro-4H-[1,3,2]dioxathiolo[4,5-c]pyran 2-oxide | 1263311-60-9

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: (3aS,4S,6R,7S,7aR)-7-fluoro-6-(fluoromethyl)-4-methoxytetrahydro-4H-[1,3,2]dioxathiolo[4,5-c]pyran 2-oxide
• CAS: 1263311-60-9
• 化学式: C₇H₁₀F₂O₅S
• 分子量: 244.216
• InChiKey: SOXFSZHHOGLNMG-RKBPOTMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  Methyl 4,6-Dideoxy-4,6-difluoro-α-D-talopyranoside 在 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 0.75h， 以44%的产率得到(3aS,4S,6R,7S,7aR)-7-fluoro-6-(fluoromethyl)-4-methoxytetrahydro-4H-[1,3,2]dioxathiolo[4,5-c]pyran 2-oxide
  参考文献：
  名称：

  Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides

  摘要：

  Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful in the fluorination of methyl 2,3,4-O-tribenzoyl -D-mannopyranoside and -D-glucopyranoside, resulting in better yields and avoiding the 1,6-methoxy migration experienced with DAST for one derivative. The two reagents gave comparable yields in the fluorination of other methyl pyranosides, confirming Deoxo-Fluor as a safer alternative to DAST. Methyl -D-mannopyranoside underwent fluorination to yield the 4,6-difluorotalopyranoside and the corresponding cyclic sulfite. The NMR spectroscopic properties of 11 benzoyl deoxy-fluoropyranosides are reported.

  DOI：

  10.1080/07328303.2010.540055