phenyl 4-O-acetyl-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-1-seleno-α-D-glucopyranoside | 1228930-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 4-O-acetyl-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-1-seleno-α-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-2-(phenylmethoxymethyl)-6-phenylselanyloxan-3-yl] acetate
• CAS: 1228930-04-8
• 化学式: C₂₇H₃₈O₆SeSi
• 分子量: 565.641
• InChiKey: ZRFMVWIYPDFRJX-ZFXZZAOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(1S,3R,4R,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-3-(phenylmethoxymethyl)-2,7-dioxabicyclo[4.1.0]heptan-4-yl] acetate 、 苯硒酚 以 四氢呋喃 为溶剂， 反应 12.0h， 以140 mg的产率得到phenyl 4-O-acetyl-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-1-seleno-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of β-Phenylselenoglycosides from Glycals and Rationalization of the Selenoglycosylation Processes

  摘要：

  beta-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe(-)) with glycals. A rationalization of the presently described beta-selectivity and the opposite alpha-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.

  DOI：

  10.1021/jo100145s