methyl 3,4-di-O-acetyl-2-bromo-2,6-dideoxy-α-L-glucopyranoside | 147028-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-2-bromo-2,6-dideoxy-α-L-glucopyranoside
• 英文别名: [(2S,3S,4R,5S,6R)-4-acetyloxy-5-bromo-6-methoxy-2-methyloxan-3-yl] acetate
• CAS: 147028-03-3
• 化学式: C₁₁H₁₇BrO₆
• 分子量: 325.156
• InChiKey: AIKHZGCPFLATHC-HLDIIMHKSA-N

物化性质

• 沸点：
  350.5±42.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-acetyl-2-bromo-2,6-dideoxy-α-L-glucopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以81%的产率得到methyl-3,4-di-O-acetyl-2,6-didesoxy-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane

  摘要：

  The stereochemistry of dehalogenation of 2-halo sugars with tributyltin hydride has been investigated in terms of the influence of steric and conformational effects using deuterium-labeling techniques. Detailed analysis of the results (Tables I-III) demonstrates that the size and orientation of the ring substituents are a determining factor in the stereochemical outcome of the reaction' However, some results can only be explained considering reduction of two equilibrating radical conformers.

  DOI：

  10.1021/jo00059a037
• 作为产物：
  描述：

  甲醇 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 4 A molecular sieve 、 溴 、 mercury dibromide 、 mercury(II) oxide 作用下， 生成 methyl 3,4-di-O-acetyl-2-bromo-2,6-dideoxy-α-L-glucopyranoside 、 methyl 3,4-di-O-acetyl-2,6-dideoxy-2-bromo-β-L-glucopyranoside 、 methyl 3,4-di-O-acetyl-2,6-dideoxy-2-bromo-α-L-mannopyranoside
  参考文献：
  名称：

  Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane

  摘要：

  The stereochemistry of dehalogenation of 2-halo sugars with tributyltin hydride has been investigated in terms of the influence of steric and conformational effects using deuterium-labeling techniques. Detailed analysis of the results (Tables I-III) demonstrates that the size and orientation of the ring substituents are a determining factor in the stereochemical outcome of the reaction' However, some results can only be explained considering reduction of two equilibrating radical conformers.

  DOI：

  10.1021/jo00059a037