phenyl-3,4,6-tri-O-methyl-β-D-glucopyranoside | 53472-80-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl-3,4,6-tri-O-methyl-β-D-glucopyranoside
• 英文别名: (2S,3R,4R,5R,6R)-4,5-dimethoxy-6-(methoxymethyl)-2-phenoxyoxan-3-ol
• CAS: 53472-80-3
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: HFXBYMORHXSLDM-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4,6-三-O-甲基-D-葡萄糖醛 、 苯酚 在 molecular sieve 、 m-chloroperbenzoic acid 、 zinc(II) chloride 作用下， 生成 phenyl-3,4,6-tri-O-methyl-β-D-glucopyranoside 、 phenyl-3,4,6-tri-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Lifetime of the glucosyl oxocarbenium ion and stereoselectivity in the glycosidation of phenols with

  摘要：

  The glycosidation of para substitued phenols with 1,2-anhydro-3,4,6-tri-O-methyl-alpha-D-glucopyranose. ZnCl2 catalysed, gives predominantly the corresponding a-anomers. In the presence of an amino base, 1.1,3,3-tetramethylguanidine. however, enhances the beta-selectivity, which becomes practically complete when the reaction is carried out under basic conditions, by addition of K2CO3 and 18-crown-6. A rationalisation based on the lifetime of the oxocarbenium ion intermediate and on the nucleophilicity of the phenols is proposed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00660-1