(6R)-β-D-glucopyranosyl 2-(2,6-dimethyl-6-vinylcyclohex-1-enyl)acetate | 1061209-66-2

• 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: (6R)-β-D-glucopyranosyl 2-(2,6-dimethyl-6-vinylcyclohex-1-enyl)acetate
• 英文别名: suspensoside A；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-[(6R)-6-ethenyl-2,6-dimethylcyclohexen-1-yl]acetate
• CAS: 1061209-66-2
• 化学式: C₁₈H₂₈O₇
• 分子量: 356.416
• InChiKey: MXCRQIIJWXVYNV-YGTFVGLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (6R)-β-D-glucopyranosyl 2-(2,6-dimethyl-6-vinylcyclohex-1-enyl)acetate
  参考文献：
  名称：

  Glucosylated Suspensosides, Water-Soluble Pheromone Conjugates from the Oral Secretions of Male Anastrepha suspensa

  摘要：

  A diastereomeric mixture of the glycosylated pheromones (6R)- (1a) and (6S)-beta-D-glucopyranosyl 2-(2,6-dimethyl-6-vinylcyclohex-1-enyl)acetate (1b), which we named respectively suspensoside A and suspensoside B. was isolated from the oral secretions of male Caribbean fruit flies, Anastrepha suspensa. The absolute stereochemical configurations were established using microsample NMR instrumentation, chiral gas chromatography, and chemical synthesis utilizing pure enantiomers of anastrephin, (3aS,4R,7aS)- (4a) or (3aR,4S,7aR)-4,7a-dimethyl-4-vinylhexahydrobenzofuran-2(3H)one (4b), its the aglycon precursor.

  DOI：

  10.1021/np800096k