(2R,3R,4R,6S)-2-(4-chloro-3-(4-methylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol | 1369405-64-0

• 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: (2R,3R,4R,6S)-2-(4-chloro-3-(4-methylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
• 英文别名: (2R,3R,4R,6S)-2-[4-chloro-3-[(4-methylphenyl)methyl]phenyl]-5,5-difluoro-6-(hydroxymethyl)oxane-3,4-diol
• CAS: 1369405-64-0
• 化学式: C₂₀H₂₁ClF₂O₄
• 分子量: 398.834
• InChiKey: VIGAWQTYBJLCNE-INDMIFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,6S)-2-(4-chloro-3-(4-methylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol 、 4-硝基苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到(2R,3S,4R,6S)-2-(4-chloro-3-(4-methylbenzyl)phenyl)-5,5-difluoro-6-(((4-nitrobenzoyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl bis(4-nitrobenzoate)
  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,4R,5S)-1,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)-3,3-difluorohexan-2-ol 在 正丁基锂 、 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 邻二氯苯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 16.0h， 生成 (2R,3R,4R,6S)-2-(4-chloro-3-(4-methylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)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

文献信息

• Synthesis and biological evaluation of SGLT2 inhibitors: gem-difluoromethylenated Dapagliflozin analogs
  作者：Zeng-Hao Chen、Ruo-Wen Wang、Feng-Ling Qing

  DOI：10.1016/j.tetlet.2012.02.062

  日期：2012.4

  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.