(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-3,3-difluoro-6-(4-methyl-3-(4-propoxybenzyl)phenyl)tetrahydro-2H-pyran | 1369405-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-3,3-difluoro-6-(4-methyl-3-(4-propoxybenzyl)phenyl)tetrahydro-2H-pyran
• CAS: 1369405-98-0
• 化学式: C₄₄H₄₆F₂O₅
• 分子量: 692.843
• InChiKey: RXTSSHKXBLTMRX-LWLZGXAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.84
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-3,3-difluoro-6-(4-methyl-3-(4-propoxybenzyl)phenyl)tetrahydro-2H-pyran 在 palladium 10% on activated carbon 、 氢气 、 邻二氯苯 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 以82%的产率得到(2R,3R,4R,6S)-5,5-difluoro-6-(hydroxymethyl)-2-(4-methyl-3-(4-propoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4-diol
  参考文献：
  名称：

  Synthesis and biological evaluation of SGLT2 inhibitors: gem-difluoromethylenated Dapagliflozin analogs

  摘要：

  Dapagliflozin is currently the most advanced SGLT2 inhibitor, which has been used in Phase III clinical trials for treatment of diabetes. Here we describe the design and synthesis of Dapagliflozin analogs modified with gem-difluoromethylene group. Their biological evaluation of in vitro inhibitory activity against human SGLT2 showed that some of the analogs with CF2 at C-4 are better SGLT2 inhibitors compared with Dapagliflozin. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.062
• 作为产物：
  描述：

  (2S,3R,5S)-2,3,6-tris(benzyloxy)-4,4-difluorohexane-1,5-diol 在 正丁基锂 、 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-3,3-difluoro-6-(4-methyl-3-(4-propoxybenzyl)phenyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Synthesis and biological evaluation of SGLT2 inhibitors: gem-difluoromethylenated Dapagliflozin analogs

  摘要：

  Dapagliflozin is currently the most advanced SGLT2 inhibitor, which has been used in Phase III clinical trials for treatment of diabetes. Here we describe the design and synthesis of Dapagliflozin analogs modified with gem-difluoromethylene group. Their biological evaluation of in vitro inhibitory activity against human SGLT2 showed that some of the analogs with CF2 at C-4 are better SGLT2 inhibitors compared with Dapagliflozin. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.062