methyl 2,3,4-tri-O-acetyl-6-deoxy-6-phenylseleno-α-D-glucopyranoside | 1622081-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-deoxy-6-phenylseleno-α-D-glucopyranoside
• CAS: 1622081-15-5
• 化学式: C₁₉H₂₄O₈Se
• 分子量: 459.355
• InChiKey: SUQOSBVHTWKYFS-FQBWVUSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside 在 rongalite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 以79%的产率得到methyl 2,3,4-tri-O-acetyl-6-deoxy-6-phenylseleno-α-D-glucopyranoside
  参考文献：
  名称：

  Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite

  摘要：

  A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.

  DOI：

  10.1016/j.carres.2014.07.011