(2S)-1-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)glycerol | 158014-07-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2S)-1-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)glycerol
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S)-1-acetyloxy-3-hydroxypropan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 158014-07-4
• 化学式: C₁₉H₂₈O₁₃
• 分子量: 464.424
• InChiKey: ZUWKJNDUAPKYGG-SWAOIJHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙酸酐-d6 、 (2S)-1-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)glycerol 在 吡啶 作用下， 反应 3.0h， 生成 (2R)-1-O-<2H3>acetyl-3-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)glycerol
  参考文献：
  名称：

  1H NMR acetyl methyl resonances of peracetylated lilioside B: a tool for the stereochemical identification of its partially acetylated derivatives

  摘要：

  Through C-13-H-1 heteronuclear shift correlation experiments all the acetyl methyl resonances of 1,3-di-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol and of the diastereoisomeric (2R) and (2S)-1-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol have been assigned in the 1H NMR spectra; partially acetylated derivatives of 2-O-(beta-D-glucopyranosyl)glycerol, Iilioside B, can so be easily identified and their configuration established also when mixtures of several derivatives are under investigation.

  DOI：

  10.1016/s0957-4166(00)86274-6
• 作为产物：
  描述：

  2-acetyloxy-1-<(acetyloxy)methyl>ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 水 作用下， 以 四氢呋喃 、 异丙醚 为溶剂， 反应 24.0h， 以34 mg的产率得到(2S)-1-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)glycerol
  参考文献：
  名称：

  Regio- and diastereoselective lipase-catalyzed preparation of acetylated 2-O-glucosylglycerols

  摘要：

  2-O-(beta-D-Glucopyranosyl) glycerol and 2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol have been submitted to lipase-catalyzed acetylation using Pseudomonas cepacia (LPS) and Candida antarctica (LCA) lipases in organic solvent. The reactions involved the glycerol moiety and were highly diastereoselective: LPS yielded the (2S)-1-O-acetylderivative, while, more interestingly, LCA yielded the (2R)-1-O-acetyl-derivative; in this way the natural compound lilioside A could be obtained. Conversely, lipase-catalyzed hydrolysis of the fully acetylated 1,3-di-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol using LCA furnished the (2S)-1-O-acetyl-derivative showing the same steric preference as the reverse reaction.

  DOI：

  10.1016/0957-4166(94)80181-9