geranyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside | 192827-18-2

• 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: geranyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-6-[(2E)-3,7-dimethylocta-2,6-dienoxy]-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 192827-18-2
• 化学式: C₃₇H₄₀O₉
• 分子量: 628.719
• InChiKey: CJIRPOPNTNSJAN-STZUOGOPSA-N

物化性质

• 沸点：
  745.0±60.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  geranyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 在 2,4,6-三甲基吡啶 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 37.0h， 生成 geraniol-1-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Naturally Occurring Geranyl 6-O-Glycosyl-b-D-glucopyranosides

  摘要：

  DOI：

  10.3987/com-05-10640
• 作为产物：
  描述：

  (2E)-3,7-二甲基-2,6-辛二烯-1-基 BETA-D-吡喃葡萄糖苷 在 盐酸 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 48.0h， 生成 geranyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Naturally Occurring Geranyl 6-O-Glycosyl-b-D-glucopyranosides

  摘要：

  DOI：

  10.3987/com-05-10640

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.
• Chemoenzymatic Synthesis of Naturally Occurring Geranyl 6-O-Glycosyl-b-D-glucopyranosides
  作者：Hiroyuki Akita、Eiji Kawahara、Mikio Fujii、Yoshiteru Ida

  DOI：10.3987/com-05-10640

  日期：——