6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose | 146197-09-3

• 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: 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose
• CAS: 146197-09-3
• 化学式: C₂₇H₂₇ClF₂O₄
• 分子量: 488.959
• InChiKey: CURYRLNBXQPDMH-BONDPLATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(三甲硅基)-1-丙醇 、 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose 在 4 A molecular sieve 、 四乙基溴化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 360.0h， 生成 、
  参考文献：
  名称：

  Synthesis and evaluation of new 6-deoxy-6-fluorinated glucosides as inhibitors of yeast α-glucosidase

  摘要：

  A series of 6-deoxy-6-fluorinated glucosides have been synthesized and evaluated as inhibitors of yeast alpha-glucosidase. These compounds have a 7- to 25-fold higher affinity than.the corresponding 6-hydroxy derivatives. The most potent inhibitor in the series was the new compound 6-deoxy-6-fluoro-(3-trimethylsilyl)propyl-alpha-D-glucopyranoside (3e) prepared by condensing 2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-alpha-D-glucosylchloride with 3-trimethylsilylpropanol.

  DOI：

  10.1016/s0022-1139(00)82408-2
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6,6-difluoro-α-D-glucopyranoside 在 盐酸 、 氯化亚砜 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.25h， 生成 6-deoxy-6,6-difluoro-2,3,4-tri-O-benzyl-1-deoxy-1-chloro-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis and evaluation of new 6-deoxy-6-fluorinated glucosides as inhibitors of yeast α-glucosidase

  摘要：

  A series of 6-deoxy-6-fluorinated glucosides have been synthesized and evaluated as inhibitors of yeast alpha-glucosidase. These compounds have a 7- to 25-fold higher affinity than.the corresponding 6-hydroxy derivatives. The most potent inhibitor in the series was the new compound 6-deoxy-6-fluoro-(3-trimethylsilyl)propyl-alpha-D-glucopyranoside (3e) prepared by condensing 2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-alpha-D-glucosylchloride with 3-trimethylsilylpropanol.

  DOI：

  10.1016/s0022-1139(00)82408-2