(3R,4S,5S,6R)-2-(4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6R)-2-(4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
• 英文别名: methyl 1-C-(4-chlorophenyl)hexopyranoside；(2S,3R,4S,5S,6R)-2-(4-chlorophenyl)-6-(hydroxymethyl)-2-methoxyoxane-3,4,5-triol
• 化学式: C₁₃H₁₇ClO₆
• 分子量: 304.727
• InChiKey: YCYZOHKCKIITCC-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R)-2-(4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 在 三乙基硅烷 、 4-二甲氨基吡啶 、 aluminum (III) chloride 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 potassium tert-butylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 53.83h， 生成 依帕列净
  参考文献：
  名称：

  Processes for the Preparation of SGLT-2 Inhibitors, Intermediates Thereof

  摘要：

  本发明涉及一种新颖的、改进的制备葡萄糖钠共转运蛋白2（SGLT-2）抑制剂及其新颖中间体的方法。更具体地说，本发明涉及一种新颖的、改进的用于制备格列列醇类化合物如恩帕格列醇和达帕格列醇及其中间体的方法。本发明的方法得到的产品可能是非晶态或结晶态，或者以非晶态/结晶态固体分散体/溶液的形式与药用可接受聚合物一起制备。此外，本发明得到的产品可用于制备用于预防和/或治疗与SGLT-2抑制相关的疾病和症状的药物。

  公开号：

  US20180346502A1
• 作为产物：
  描述：

  葡萄糖酸内酯 在 N-甲基吗啉 、 正丁基锂 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (3R,4S,5S,6R)-2-(4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Processes for the Preparation of SGLT-2 Inhibitors, Intermediates Thereof

  摘要：

  本发明涉及一种新颖的、改进的制备葡萄糖钠共转运蛋白2（SGLT-2）抑制剂及其新颖中间体的方法。更具体地说，本发明涉及一种新颖的、改进的用于制备格列列醇类化合物如恩帕格列醇和达帕格列醇及其中间体的方法。本发明的方法得到的产品可能是非晶态或结晶态，或者以非晶态/结晶态固体分散体/溶液的形式与药用可接受聚合物一起制备。此外，本发明得到的产品可用于制备用于预防和/或治疗与SGLT-2抑制相关的疾病和症状的药物。

  公开号：

  US20180346502A1

文献信息

• Process For Production Of 4-Biphenylyazetidin-2-Ones
  申请人：Lee Peter

  公开号：US20080287663A1

  公开（公告）日：2008-11-20

  The present invention relates to processes for the production of 4-biphenylylazetidin-2-one derivatives of formula

  本发明涉及生产4-联苯基氮杂环己烷-2-酮衍生物的方法。
• Processes for the preparation of SGLT-2 inhibitors, intermediates thereof
  申请人：Emmennar Pharma Private Limited

  公开号：US10703772B2

  公开（公告）日：2020-07-07

  The present invention relates to novel, improved processes for the preparation of sodium glucose co-transporter 2 (SGLT-2) inhibitors and novel intermediates thereof. More particularly, the present invention relates to a novel, improved process for the preparation of gliflozin compounds such as empagliflozin and dapagliflozin, intermediates thereof. The product obtained from the processes of present invention may be amorphous or crystalline, or in the form of amorphous/crystalline solid dispersions/solutions with pharmaceutically acceptable polymers and preparation process thereof. Also, the products obtained from the present invention may be used for the preparation of medicaments for the prevention and/or treatment of diseases and conditions associated with SGLT-2 inhibition.

  本发明涉及制备钠葡萄糖共转运体2（SGLT-2）抑制剂及其新型中间体的新型改进工艺。更具体地说，本发明涉及一种制备格列洛嗪化合物（如empagliflozin和dapagliflozin）及其中间体的新型改进工艺。从本发明工艺中获得的产品可以是无定形或结晶，或以无定形/结晶固体分散体/溶液的形式与药学上可接受的聚合物及其制备工艺一起存在。此外，本发明所得产品还可用于制备预防和/或治疗与 SGLT-2 抑制有关的疾病和病症的药物。
• Remarkable β-Selectivity in the Synthesis of β-1-<i>C</i>-Arylglucosides:  Stereoselective Reduction of Acetyl-Protected Methyl 1-<i>C</i>-Arylglucosides without Acetoxy-Group Participation
  作者：Prashant P. Deshpande、Bruce A. Ellsworth、Frederic G. Buono、Annie Pullockaran、Janak Singh、Thomas P. Kissick、Ming-H. Huang、Hildegard Lobinger、Theodor Denzel、Richard H. Mueller

  DOI：10.1021/jo071051i

  日期：2007.12.1

  [GRAPHICS]An efficient and practical process to generate beta-C-arylglucoside derivatives was achieved. The process described involves Lewis acid mediated ionic reduction of a peracetylated 1-C-aryl methyl glucoside derived from the addition of an aryl-Li to selectively protected delta-D-gluconolactone. The reduction of the 2-acetoxy-1-C-oxacarbenium ion intermediates proceeds with a high degree of selectivity to give beta-C-arylglucosides without 2-acetoxy group participation. Furthermore, during the reduction process we also identified an unprecedented critical role of water. By changing from the usual benzyl ether protecting groups because of cost and chemical compatibility concerns, the new process is made additionally efficient and highly selective.
• Processes for the Preparation of SGLT-2 Inhibitors, Intermediates Thereof
  申请人：Emmennar Pharma Private Limited

  公开号：US20180346502A1

  公开（公告）日：2018-12-06

  The present invention relates to novel, improved processes for the preparation of sodium glucose co-transporter 2 (SGLT-2) inhibitors and novel intermediates thereof. More particularly, the present invention relates to a novel, improved process for the preparation of gliflozin compounds such as empagliflozin and dapagliflozin, intermediates thereof. The product obtained from the processes of present invention may be amorphous or crystalline, or in the form of amorphous/crystalline solid dispersions/solutions with pharmaceutically acceptable polymers and preparation process thereof. Also, the products obtained from the present invention may be used for the preparation of medicaments for the prevention and/or treatment of diseases and conditions associated with SGLT-2 inhibition.

  本发明涉及一种新颖的、改进的制备葡萄糖钠共转运蛋白2（SGLT-2）抑制剂及其新颖中间体的方法。更具体地说，本发明涉及一种新颖的、改进的用于制备格列列醇类化合物如恩帕格列醇和达帕格列醇及其中间体的方法。本发明的方法得到的产品可能是非晶态或结晶态，或者以非晶态/结晶态固体分散体/溶液的形式与药用可接受聚合物一起制备。此外，本发明得到的产品可用于制备用于预防和/或治疗与SGLT-2抑制相关的疾病和症状的药物。