3-氧代-3-[[(2R,3S,4S,5R,6S)-3,4,5-三羟基-6-(苯氧基)四氢吡喃-2-基]甲氧基]丙酸 | 104932-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氧代-3-[[(2R,3S,4S,5R,6S)-3,4,5-三羟基-6-(苯氧基)四氢吡喃-2-基]甲氧基]丙酸
• 中文别名: 4-苯基-6-O-丙二酰葡萄糖苷
• 英文名称: phenyl 6'-O-malonyl-β-D-glucopyranoside
• 英文别名: 4-Phenyl-6-O-malonylglucoside；3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-phenoxyoxan-2-yl]methoxy]propanoic acid
• CAS: 104932-60-7
• 化学式: C₁₅H₁₈O₉
• 分子量: 342.303
• InChiKey: WROCAMQDRXZFKS-SWMGHYKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  丙二酸 、 苯基-BETA-葡萄糖吡喃糖苷 在 叔丁基异氰酸酯 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以59%的产率得到3-氧代-3-[[(2R,3S,4S,5R,6S)-3,4,5-三羟基-6-(苯氧基)四氢吡喃-2-基]甲氧基]丙酸
  参考文献：
  名称：

  Synthesis of Phenyl 6‘-O-Malonyl-β-d-glucopyranoside. Facile Preparation of Malonylated Glycoconjugates

  摘要：

  Regioselective acylation of glycoconjugates with malonic acid was achieved by suing phenyl beta-D-glucopyranoside as a model glycoside, malonic acid, and tert-butyl isocyanide in aprotic solvents. Structural elucidation of phenyl 6'-O-malonyl-beta-D-glucopyranoside was performed by H-1 and C-13 NMR spectroscopy and high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry; (HPLC-APCI-MS/MS). This one-step reaction opens the way to the preparation of reference substances which are required for the spectroscopic identification of malonylated glycosides in complex natural matrices.

  DOI：

  10.1021/jf950827q

文献信息

• Synthesis of Phenyl 6‘-<i>O</i>-Malonyl-β-<scp>d</scp>-glucopyranoside. Facile Preparation of Malonylated Glycoconjugates
  作者：René Roscher、Jens-Peter Steffen、Markus Herderich、Wilfried Schwab、Peter Schreier

  DOI：10.1021/jf950827q

  日期：1996.1.1

  Regioselective acylation of glycoconjugates with malonic acid was achieved by suing phenyl beta-D-glucopyranoside as a model glycoside, malonic acid, and tert-butyl isocyanide in aprotic solvents. Structural elucidation of phenyl 6'-O-malonyl-beta-D-glucopyranoside was performed by H-1 and C-13 NMR spectroscopy and high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry; (HPLC-APCI-MS/MS). This one-step reaction opens the way to the preparation of reference substances which are required for the spectroscopic identification of malonylated glycosides in complex natural matrices.