Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-bromo-phenylsulfanyl)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester | 881848-67-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-bromo-phenylsulfanyl)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
• CAS: 881848-67-5
• 化学式: C₃₂H₃₉BrO₁₇S
• 分子量: 807.621
• InChiKey: RGQKXWSOPKSLRN-AJUMBUHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  51.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-bromo-phenylsulfanyl)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3

  摘要：

  Phase transfer catalyzed reaction was used for the high yielding synthesis of aryl 1-thio-beta-D-galacto- and lacto-pyranosides carrying a panel of substituents on the phenyl groups. Best galectin-1 inhibitors were simple p-nitrophenyl thiogalactoside 5a for the monosaccharide and o-nitrophenyl thiolactoside 6f or napthylsulfonyl lactoside 8c, both being 20 times better relative to natural ligands. Relative inhibitory properties as low as 2500 and 40 mu M were observed, respectively. The electronic effects of the lactoside aglycons directly influenced the electrostatic potential at O-3, which was associated with the inhibitory potencies against galectin-1. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.010
• 作为产物：
  描述：

  lactose octaacetate 在 氢溴酸 、 四丁基硫酸氢铵 、 sodium carbonate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-bromo-phenylsulfanyl)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3

  摘要：

  Phase transfer catalyzed reaction was used for the high yielding synthesis of aryl 1-thio-beta-D-galacto- and lacto-pyranosides carrying a panel of substituents on the phenyl groups. Best galectin-1 inhibitors were simple p-nitrophenyl thiogalactoside 5a for the monosaccharide and o-nitrophenyl thiolactoside 6f or napthylsulfonyl lactoside 8c, both being 20 times better relative to natural ligands. Relative inhibitory properties as low as 2500 and 40 mu M were observed, respectively. The electronic effects of the lactoside aglycons directly influenced the electrostatic potential at O-3, which was associated with the inhibitory potencies against galectin-1. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.010