4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1R)-3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose | 358369-24-1

• 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: 4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1R)-3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(R)-[(1R,2R,4R,5S,6R)-5-acetyloxy-3,8,9-trioxatricyclo[4.2.1.02,4]nonan-4-yl]-fluoromethyl]oxan-2-yl]methyl acetate
• CAS: 358369-24-1
• 化学式: C₂₃H₂₉FO₁₄
• 分子量: 548.473
• InChiKey: NZKRVOQQOJSFGR-SYRZMUPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  172
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1R)-3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose 在 氨 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 2,3-anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-furanose
  参考文献：
  名称：

  Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-d-glycero-d-gulo- heptitol-1-C-yl]-β-d-gulo-furanose:  First Example of a Monofluoromethylene-Linked C-Disaccharide

  摘要：

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

  DOI：

  10.1021/jo0102462
• 作为产物：
  描述：

  乙酸酐 、 1,6:2,3-dianhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 15.0h， 以96%的产率得到4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1R)-3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
  参考文献：
  名称：

  Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-d-glycero-d-gulo- heptitol-1-C-yl]-β-d-gulo-furanose:  First Example of a Monofluoromethylene-Linked C-Disaccharide

  摘要：

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

  DOI：

  10.1021/jo0102462