3-hydroxy-2-methylbuntanenitrile β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-2-methylbuntanenitrile β-D-glucopyranoside
• 英文别名: NCGC00385866-02_C11H19NO6_3-(beta-D-Glucopyranosyloxy)-2-methylbutanenitrile；2-methyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanenitrile
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: LHNFRFAOVVPESM-IQACCLBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,3S)-3-hydroxy-2-methylbutanenitrile β-D-glucopyranoside 6′-O-(2″S,3″R)-2″-ethyl-2″,3″-dihydroxybutyrate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以2 mg的产率得到3-hydroxy-2-methylbuntanenitrile β-D-glucopyranoside
  参考文献：
  名称：

  Microtropins A–I: 6′-O-(2″S,3″R)-2″-Ethyl-2″,3″-dihydroxybutyrates of aliphatic alcohol β-d-glucopyranosides from the branches of Microtropis japonica

  摘要：

  From the branches of Microtropis japonica (Celastraceae), nine aliphatic glucosides, named microtropins A-I, were isolated. The 6-position of glucose was esterified with (2S,3R)-2-ethyl-2,3-dihydroxybutyric acid. Microtropins A-D contained a rare natured product nitrile functional group in their aglycones. The absolute structures of the (25,3R)-2-ethyl-2,3-dihydroxybutyric acid moiety and aglycone of microtropin A were determined by an X-ray crystallographic method. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.11.007

文献信息

• Microtropins A–I: 6′-O-(2″S,3″R)-2″-Ethyl-2″,3″-dihydroxybutyrates of aliphatic alcohol β-d-glucopyranosides from the branches of Microtropis japonica
  作者：Yuka Uemura、Sachiko Sugimoto、Katsuyoshi Matsunami、Hideaki Otsuka、Yoshio Takeda、Masatoshi Kawahata、Kentaro Yamaguchi

  DOI：10.1016/j.phytochem.2012.11.007

  日期：2013.3

  From the branches of Microtropis japonica (Celastraceae), nine aliphatic glucosides, named microtropins A-I, were isolated. The 6-position of glucose was esterified with (2S,3R)-2-ethyl-2,3-dihydroxybutyric acid. Microtropins A-D contained a rare natured product nitrile functional group in their aglycones. The absolute structures of the (25,3R)-2-ethyl-2,3-dihydroxybutyric acid moiety and aglycone of microtropin A were determined by an X-ray crystallographic method. (C) 2012 Elsevier Ltd. All rights reserved.