(2S,3R,4S,5R,6R)-2-((3,7-dimethylocta-1,6-dien-3-yl)oxy)-6-((((2R,3R,4S,5S)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 192827-23-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,4S,5R,6R)-2-((3,7-dimethylocta-1,6-dien-3-yl)oxy)-6-((((2R,3R,4S,5S)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS: 192827-23-9
• 化学式: C₆₃H₆₀O₁₆
• 分子量: 1073.16
• InChiKey: HGBOXVNADDGEBU-ZBZPDEMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.15
• 重原子数：
  79.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  194.72
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-2-((3,7-dimethylocta-1,6-dien-3-yl)oxy)-6-((((2R,3R,4S,5S)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以90%的产率得到Linalyl beta-vicianoside
  参考文献：
  名称：

  The Role of Diglycosides as Tea Aroma Precursors:  Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves

  摘要：

  Two general synthetic routes were established in order to synthesize two diglycosides, primeverosides (1) and vicianosides (2), found in tea leaves. Procedure 1 is based on the Koenig-Knorr type of condensation of aglycon alcohols and 1-alpha-bromohexabenzoylprimeverose (6) and is suitable for the condensation of primary alcohols. Procedure 2 is to combine tribenzoyl-beta-D-glucoside (8) and 1-alpha-bromotribenzoylxylose (4). The primeveroside of a tertiary alcohol was synthesized by this method which is also applicable to the synthesis of vicianosides. The hydrolysis rate of each of the 12 synthesized glycosides by a crude tea enzyme was evaluated, which suggest that the main glycosidase is primeverosidase and the enzyme mixture shows substrate specificity to both the carbohydrate and aglycon moieties.

  DOI：

  10.1021/jf960852b
• 作为产物：
  描述：

  1,2,3,4-tetra-O-benzoyl-β-L-arabinopyranose 在 氢溴酸 、 氰化汞 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 (2S,3R,4S,5R,6R)-2-((3,7-dimethylocta-1,6-dien-3-yl)oxy)-6-((((2R,3R,4S,5S)-3,4,5-tris(benzoyloxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  The Role of Diglycosides as Tea Aroma Precursors:  Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves

  摘要：

  Two general synthetic routes were established in order to synthesize two diglycosides, primeverosides (1) and vicianosides (2), found in tea leaves. Procedure 1 is based on the Koenig-Knorr type of condensation of aglycon alcohols and 1-alpha-bromohexabenzoylprimeverose (6) and is suitable for the condensation of primary alcohols. Procedure 2 is to combine tribenzoyl-beta-D-glucoside (8) and 1-alpha-bromotribenzoylxylose (4). The primeveroside of a tertiary alcohol was synthesized by this method which is also applicable to the synthesis of vicianosides. The hydrolysis rate of each of the 12 synthesized glycosides by a crude tea enzyme was evaluated, which suggest that the main glycosidase is primeverosidase and the enzyme mixture shows substrate specificity to both the carbohydrate and aglycon moieties.

  DOI：

  10.1021/jf960852b