Linalyl beta-vicianoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Linalyl beta-vicianoside
• 英文别名: (2S,3R,4S,5S,6R)-2-(3,7-dimethylocta-1,6-dien-3-yloxy)-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• 化学式: C₂₁H₃₆O₁₀
• 分子量: 448.511
• InChiKey: OKNPZRJNRSGKME-AVIYVUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-β-L-arabinopyranosyl bromide 在 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.0h， 生成 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

文献信息

• The Role of Diglycosides as Tea Aroma Precursors:  Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves
  作者：Sachiko Matsumura、Shunya Takahashi、Mariko Nishikitani、Kikue Kubota、Akio Kobayashi

  DOI：10.1021/jf960852b

  日期：1997.7.1

  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.