methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-galactopyranoside | 1263311-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-galactopyranoside
• 英文别名: [(2S,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-(fluoromethyl)-6-methoxyoxan-3-yl] benzoate
• CAS: 1263311-55-2
• 化学式: C₂₈H₂₅FO₈
• 分子量: 508.5
• InChiKey: NXMRHTRUMFEGCN-SUWSLWCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 吡啶 、 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 水 、 磷脂酶B 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-galactopyranoside
  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

文献信息

• Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides
  作者：Aslan M. Esmurziev、Nebojsa Simic、Bård Helge Hoff、Eirik Sundby

  DOI：10.1080/07328303.2010.540055

  日期：2010.9

  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.