1-(β-D-glucopyranosyl)-2,3-(2S)-propanediol | 54503-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-glucopyranosyl)-2,3-(2S)-propanediol
• 英文别名: (2S,3R,4R,5S,6R)-2-[(2S)-2,3-dihydroxypropyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 54503-51-4
• 化学式: C₉H₁₈O₇
• 分子量: 238.238
• InChiKey: PRRKMHMJORXPQU-JITZTYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2S)-1-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)-2,3-propanediol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 43.0h， 以10.3 mg的产率得到1-(β-D-glucopyranosyl)-2,3-(2S)-propanediol
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 6. Conformational similarity of glycosides and corresponding C-glycosides

  摘要：

  The conformation of the alpha-(axial)-C-glycosides 1-3 and the beta-(equatorial)-C-glycosides 4-6 were studied by H-1 NMR. Their preferred solution conformation was found to match that of the corresponding parent glycosides. The study of 2-deoxy compounds 13-16 shows that the preference is due primarily to gauche interactions around the glycosidic bond. Solvent studies indicate that electrostatic interactions and hydrogen bonds do not significantly alter the overall conformation. Temperature studies suggest that these compounds exist as an equilibrium mixture of conformers.

  DOI：

  10.1021/jo00022a038

文献信息

• Preferred conformation of C-glycosides. 6. Conformational similarity of glycosides and corresponding C-glycosides
  作者：Peter G. Goekjian、Tse Chong Wu、Yoshito Kishi

  DOI：10.1021/jo00022a038

  日期：1991.10

  The conformation of the alpha-(axial)-C-glycosides 1-3 and the beta-(equatorial)-C-glycosides 4-6 were studied by H-1 NMR. Their preferred solution conformation was found to match that of the corresponding parent glycosides. The study of 2-deoxy compounds 13-16 shows that the preference is due primarily to gauche interactions around the glycosidic bond. Solvent studies indicate that electrostatic interactions and hydrogen bonds do not significantly alter the overall conformation. Temperature studies suggest that these compounds exist as an equilibrium mixture of conformers.