2-Acetyl-2-((2S,5S,6R)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-3-oxo-butyric acid methyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetyl-2-((2S,5S,6R)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-3-oxo-butyric acid methyl ester
• 英文别名: methyl 2-acetyl-2-[(2S,5S,6R)-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]-3-oxobutanoate
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: HQKFDJRNALLUMR-AXFHLTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-Acetyl-2-((2S,5S,6R)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-3-oxo-butyric acid methyl ester 在 吡啶 作用下， 反应 12.0h， 生成 methyl 2-(4',6'-di-O-acetyl-2',3'-dideoxy-D-erythro-hexopyranosyl)-2,2-diacetylacetate
  参考文献：
  名称：

  Assignment of anomeric configuration of C-glycopyranosides and C-glycofuranosides. A proton, carbon-13, and nuclear Overhauser enhancement spectrometric study

  摘要：

  The utility of H-1, C-13, and nuclear Overhauser enhancement spectrometries for assignment of C-glycopyranosides and C-glycofuranosides to alpha or beta anomer series has been assessed. Specifically examined were H-1-H-1 coupling constants J1',2' and J4',5', H-1 chemical shifts delta(H1'), C-13 chemical shifts delta(C1') and delta(C5'), H-1-C-13 coupling constants J(C1',H1'), and nuclear Overhauser effects (NOE) observed upon irradiation of H1', H4', and H5'. While all of these data have been used for assignment of anomeric configuration of C-glycosides, this study demonstrates that the NOE obtained by irradiation of H1' is uniquely reliable. For beta C-glycosides, in which H1' and H5' (C-glycopyranosides) or H1' and H4' (C-glycofuranosides) are on the same face of the carbohydrate ring, irradiation of H1' gives rise to the appropriate NOE. In no instance does irradiation of an a C-glycoside give rise to such an effect.

  DOI：

  10.1021/jo00063a015
• 作为产物：
  描述：

  methyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-D-erythro-hexopyranosyl)-2,2-diacetylacetate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 12.0h， 生成 2-Acetyl-2-((2S,5S,6R)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-3-oxo-butyric acid methyl ester
  参考文献：
  名称：

  Assignment of anomeric configuration of C-glycopyranosides and C-glycofuranosides. A proton, carbon-13, and nuclear Overhauser enhancement spectrometric study

  摘要：

  The utility of H-1, C-13, and nuclear Overhauser enhancement spectrometries for assignment of C-glycopyranosides and C-glycofuranosides to alpha or beta anomer series has been assessed. Specifically examined were H-1-H-1 coupling constants J1',2' and J4',5', H-1 chemical shifts delta(H1'), C-13 chemical shifts delta(C1') and delta(C5'), H-1-C-13 coupling constants J(C1',H1'), and nuclear Overhauser effects (NOE) observed upon irradiation of H1', H4', and H5'. While all of these data have been used for assignment of anomeric configuration of C-glycosides, this study demonstrates that the NOE obtained by irradiation of H1' is uniquely reliable. For beta C-glycosides, in which H1' and H5' (C-glycopyranosides) or H1' and H4' (C-glycofuranosides) are on the same face of the carbohydrate ring, irradiation of H1' gives rise to the appropriate NOE. In no instance does irradiation of an a C-glycoside give rise to such an effect.

  DOI：

  10.1021/jo00063a015