4,6-di-O-benzyl-3-deoxy-1,2-O-(1-ethoxyethylidene)-3-fluoro-α-D-glucopyranose | 187218-53-7

• 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: 4,6-di-O-benzyl-3-deoxy-1,2-O-(1-ethoxyethylidene)-3-fluoro-α-D-glucopyranose
• CAS: 187218-53-7
• 化学式: C₂₄H₂₉FO₆
• 分子量: 432.489
• InChiKey: AIGAXSUAJBOSKW-WLISMNNQSA-N

物化性质

• 沸点：
  515.7±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,6-di-O-benzyl-3-deoxy-1,2-O-(1-ethoxyethylidene)-3-fluoro-α-D-glucopyranose 在 溶剂黄146 作用下， 反应 1.5h， 生成 Acetic acid (2S,3S,4S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-4-fluoro-2-hydroxy-tetrahydro-pyran-3-yl ester 、 Acetic acid (2R,3S,4R,5R,6R)-5-benzyloxy-6-benzyloxymethyl-4-fluoro-3-hydroxy-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  Synthesis of glycyrrhizin analogues containing fluorinated β(1→2)-linked disaccharides

  摘要：

  For studies on the recognition mechanisms for Glycyrrhizin-induced biological activities, seven Glycyrrhizin analogues with 3'-,4'-,6'-,3-, and 4-fluorinated 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoses (1-5) and 3- and 4-fluorinated 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranoses (6 and 7) were synthesized through a stepwise glycosylation procedure. 1,2-Di-O-acetyl-4,6-di-0-benzyl-3-deoxy-3-fluoro- (13) and 1,2-di-O-acetyl-3,6-di-O-benzyl-4-deoxy-4-fluoro-D-glucopyranose (14) were employed for the first beta-glycosylation of methyl glycyrrhetate, promoted with trimethylsilyl trifluoromethanesulfonate. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00169-1
• 作为产物：
  描述：

  在 2,4,6-三甲基吡啶 、 四丁基溴化铵 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4,6-di-O-benzyl-3-deoxy-1,2-O-(1-ethoxyethylidene)-3-fluoro-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of glycyrrhizin analogues containing fluorinated β(1→2)-linked disaccharides

  摘要：

  For studies on the recognition mechanisms for Glycyrrhizin-induced biological activities, seven Glycyrrhizin analogues with 3'-,4'-,6'-,3-, and 4-fluorinated 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoses (1-5) and 3- and 4-fluorinated 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranoses (6 and 7) were synthesized through a stepwise glycosylation procedure. 1,2-Di-O-acetyl-4,6-di-0-benzyl-3-deoxy-3-fluoro- (13) and 1,2-di-O-acetyl-3,6-di-O-benzyl-4-deoxy-4-fluoro-D-glucopyranose (14) were employed for the first beta-glycosylation of methyl glycyrrhetate, promoted with trimethylsilyl trifluoromethanesulfonate. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00169-1