(1R,2R)-1-[(4S)-5,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1,3-dithian-2-yl]ethane-1,2-diol | 1233482-00-2

• 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: (1R,2R)-1-[(4S)-5,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1,3-dithian-2-yl]ethane-1,2-diol
• CAS: 1233482-00-2
• 化学式: C₂₈H₃₇ClO₇S₂
• 分子量: 585.183
• InChiKey: FOKGLKRZVADGIX-SDHSZQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-[(4S)-5,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1,3-dithian-2-yl]ethane-1,2-diol 在 三氟乙酸 作用下， 反应 96.0h， 以491 mg的产率得到埃格列净
  参考文献：
  名称：

  Stereoselective Synthesis of a Dioxa-bicyclo[3.2.1]octane SGLT2 Inhibitor

  摘要：

  A promising class of SGLT2 inhibitors bearing a unique dioxa-bicyclo[3.2.1]octane motif was recently disclosed. An improved stereoselective synthesis providing efficient access to one of the most potent and selective compounds from this class is reported. A one-pot deprotection/cyclization was used as the key step to form the dioxa-bicyclo[3.2.1]octane motif with full control of stereochemistry. Using an appropriately substituted aryl group, the route enables the synthesis of any given compound from the class.

  DOI：

  10.1021/ol100940w
• 作为产物：
  描述：

  (3aS,6aS)-6-((R)-(2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1,3-dithian-2-yl)(hydroxy)methyl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol 在 sodium tetrahydroborate 、 水 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成 (1R,2R)-1-[(4S)-5,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1,3-dithian-2-yl]ethane-1,2-diol
  参考文献：
  名称：

  Stereoselective Synthesis of a Dioxa-bicyclo[3.2.1]octane SGLT2 Inhibitor

  摘要：

  A promising class of SGLT2 inhibitors bearing a unique dioxa-bicyclo[3.2.1]octane motif was recently disclosed. An improved stereoselective synthesis providing efficient access to one of the most potent and selective compounds from this class is reported. A one-pot deprotection/cyclization was used as the key step to form the dioxa-bicyclo[3.2.1]octane motif with full control of stereochemistry. Using an appropriately substituted aryl group, the route enables the synthesis of any given compound from the class.

  DOI：

  10.1021/ol100940w

文献信息

• Acta Cryst. 2010, E66, o1386
  作者：

  DOI：——

  日期：——
• J. Chem. Soc. Perkin Trans. 1 1987, 21-26
  作者：

  DOI：——

  日期：——
• Org. Lett. 2010, 12, 2940-2943
  作者：

  DOI：——

  日期：——
• Stereoselective Synthesis of a Dioxa-bicyclo[3.2.1]octane SGLT2 Inhibitor
  作者：Vincent Mascitti、Cathy Préville

  DOI：10.1021/ol100940w

  日期：2010.7.2

  A promising class of SGLT2 inhibitors bearing a unique dioxa-bicyclo[3.2.1]octane motif was recently disclosed. An improved stereoselective synthesis providing efficient access to one of the most potent and selective compounds from this class is reported. A one-pot deprotection/cyclization was used as the key step to form the dioxa-bicyclo[3.2.1]octane motif with full control of stereochemistry. Using an appropriately substituted aryl group, the route enables the synthesis of any given compound from the class.