(1S,2R,5S)-menthyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside | 768368-82-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,5S)-menthyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: (-)-menthyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 768368-82-7
• 化学式: C₃₇H₄₈O₆
• 分子量: 588.785
• InChiKey: SDOKOQNRRQRYSZ-RKIGANGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S)-menthyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 在 乙酸酐 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Experimental evidence on the hydroxymethyl group conformation in alkyl β-d-mannopyranosides

  摘要：

  A rotational population Study of the hydroxymethyl group of alkyl beta-D-mannopyranosides was performed by means of CD and NMR spectroscopy. Three different benzyl, acetyl, and p-bromobenzoyl series of alkyl beta-D-mannopyranosides with different chiral and nonchiral aglycons were synthesized and analyzed. Different rotational populations were observed for each series by changing the structure of the aglycon. The results showed a clear correlation between the rotational population of the hydroxymethyl group around the C5-C6 bond and the pK(a) of the bonded alcohol (aglycon). The population of the gt rotamer gradually increased as the pK(a) increased while that of the gg rotamer decreased and the population of the tg rotamer remained almost constant. This is explained by the exo-anomeric effect. For chiral alkyl derivatives, the results also showed a close dependence on the absolute configuration of the aglycon. Comparison of rotational population anomers revealed the dependence or the hydroxymethyl group on the anomeric configuration and a greater dependence on the aglycon structure in the beta anomers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.019
• 作为产物：
  描述：

  D-薄荷醇 、 3,4,6-tri-O-benzyl-D-glucal epoxide 以 乙酸乙酯 为溶剂， 反应 8.0h， 以88%的产率得到(1S,2R,5S)-menthyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  在中性条件下使用1,2-脱水糖进行简单温和的立体选择性O-糖基化

  摘要：

  的开环α - d -1,2- anhydrohexapyranoses与酚在没有金属离子的催化剂或添加剂在乙酸乙酯（中性条件）顺利进行立体选择性配料1,2-顺式- α -芳基糖苷作为主要产物和1,2-反式- β -芳基苷作为良好收益次要产物。在相似的条件下，这种与醇的开环反应以优异的产率仅提供β-烷基糖苷。

  DOI：

  10.1016/j.tetlet.2019.01.049