1,2-O-isopropylidene-3,6-di-O-methylsulfonyl-α-D-glucofuranose | 190001-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3,6-di-O-methylsulfonyl-α-D-glucofuranose
• CAS: 190001-96-8
• 化学式: C₁₁H₂₀O₁₀S₂
• 分子量: 376.406
• InChiKey: MOHIQOWDOJRVFB-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.46
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  134.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3,6-di-O-methylsulfonyl-α-D-glucofuranose 在 Amberlite IR 120 (H⁺) ion exchange resin 、 水 作用下， 生成 3,6-di-O-methylsulfonyl-D-glucose 、 3,6-di-O-methylsulfonyl-D-glucose
  参考文献：
  名称：

  Synthesis of O-methylsulfonyl derivatives of d-glucose as potential alkylating agents for targeted drug delivery to the brain. Evaluation of their interaction with the human erythrocyte GLUT1 hexose transporter

  摘要：

  In order to obtain hydrophilic analogues of 1,4-dimethylsulfonyloxybutane (busulfan) with enhanced selectivity and improved brain penetration, we have synthesized 6-O-methylsulfonyl-D-glucose, 3-O-methylsulfonyl-D-glucose, 3,6-di-O-methylsulfonyl-D-glucose, 4-O-methylsulfonyl-D-glucose, and 4,6-di-O-methylsulfonyl-D-glucose, and we have studied their interactions with the human erythrocyte GLUT1 hexose transport system. Mesylation of OH-4 and OH-6 of glucose resulted in a slightly diminished affinity for the GLUT1 glucose transporter, whereas mesylation of OH-3 led to complete loss of affinity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00328-x
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-3-O-(甲磺酰基)-alpha-D-呋喃葡萄糖 在 吡啶 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 1,2-O-isopropylidene-3,6-di-O-methylsulfonyl-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of O-methylsulfonyl derivatives of d-glucose as potential alkylating agents for targeted drug delivery to the brain. Evaluation of their interaction with the human erythrocyte GLUT1 hexose transporter

  摘要：

  In order to obtain hydrophilic analogues of 1,4-dimethylsulfonyloxybutane (busulfan) with enhanced selectivity and improved brain penetration, we have synthesized 6-O-methylsulfonyl-D-glucose, 3-O-methylsulfonyl-D-glucose, 3,6-di-O-methylsulfonyl-D-glucose, 4-O-methylsulfonyl-D-glucose, and 4,6-di-O-methylsulfonyl-D-glucose, and we have studied their interactions with the human erythrocyte GLUT1 hexose transport system. Mesylation of OH-4 and OH-6 of glucose resulted in a slightly diminished affinity for the GLUT1 glucose transporter, whereas mesylation of OH-3 led to complete loss of affinity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00328-x