2-{[4-(methyloxy)phenyl]methyl}phenyl-6-O-[(methyloxy)carbonyl]-β-D-glucopyranoside | 408504-27-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{[4-(methyloxy)phenyl]methyl}phenyl-6-O-[(methyloxy)carbonyl]-β-D-glucopyranoside
• 英文别名: 2-(4-methoxybenzyl)phenyl 6-O-methoxycarbonyl-β-D-glucopyranoside；methyl [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(4-methoxyphenyl)methyl]phenoxy]oxan-2-yl]methyl carbonate
• CAS: 408504-27-8
• 化学式: C₂₂H₂₆O₉
• 分子量: 434.443
• InChiKey: UDDYQZYXJSDBIS-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-羟基甲基-6-[2-(4-甲氧基-苄基)-苯氧基]-四氢-吡喃-3,4,5-三醇 、 二甲基二碳酸盐 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 14.0h， 以59%的产率得到2-{[4-(methyloxy)phenyl]methyl}phenyl-6-O-[(methyloxy)carbonyl]-β-D-glucopyranoside
  参考文献：
  名称：

  由三氟甲磺酸钪 (III) 催化介导的未保护吡喃糖衍生物的高选择性初级烷氧基羧化和酯化

  摘要：

  描述了一种用于吡喃糖衍生物的伯醇的烷氧基羧化和酰化的高选择性方法。该反应产率高，在温和条件下进行，0.15-1 mol-% Sc(OTf)3 与酸酐或焦碳酸盐结合使用，温度为 40-50 °C。观察到的未保护吡喃糖衍生物的烷氧基羧化选择性 > 95%，这构成了优于现有方法的显着优势。还讨论了机械影响，包括空间需求和金属-杂原子配位的作用。

  DOI：

  10.1002/ejoc.201200261

文献信息

• Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing the same
  申请人：——

  公开号：US20040018998A1

  公开（公告）日：2004-01-29

  The present invention relates to glucopyranosyloxybenzylbenzene derivatives represented by the general formula: 1 wherein P represents a group forming a prodrug; and R represents a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkoxy-substituted (lower alkyl) group, a lower alkoxy-substituted (lower alkoxy) group or a lower alkoxy-substituted (lower alkylthio) group, which have an improved oral absorption and can exert an excellent inhibitory activity in human SGLT2 in vivo and which are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications or obesity, and pharmaceutical compositions comprising the same.

  本发明涉及由通式表示的葡萄糖吡喃基氧基苯基苄基苯基衍生物：其中P代表形成前药的基团；R代表下位烷基基团、下位烷氧基基团、下位烷基硫基团、下位烷氧基取代的（下位烷基）基团、下位烷氧基取代的（下位烷氧基）基团或下位烷氧基取代的（下位烷基硫）基团，这些衍生物具有改善的口服吸收能力，在人体SGLT2中可以发挥出色的抑制活性，对于预防或治疗与高血糖相关的疾病，如糖尿病、糖尿病并发症或肥胖症等，以及包含这些衍生物的药物组合物，具有应用价值。
• PROGRESSION INHIBITOR FOR DISEASE ATTRIBUTED TO ABNORMAL ACCUMULATION OF LIVER FAT
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1782828A1

  公开（公告）日：2007-05-09

  The present invention provides pharmaceutical compositions useful as agents for the inhibition of progression of diseases associated with abnormal accumulation ofliverlipids. In particular, the pharmaceutical compositions of the present invention which comprise as an active ingredient a sodium/glucose co-transporter 2 inhibitor are highly suitable as an agent for the inhibition of progression of not only common fatty liver but also non-alcholic fatty liver disease (NAFL), non-alcholic steatohepatitis (NASH), hypernutritive fatty liver, diabetic fatty liver, alcholic fatty liver disease toxic fatty liver or the like.

  本发明提供的药物组合物可作为抑制与肝脂异常积聚有关的疾病进展的药物。特别是，本发明的药物组合物包含钠/葡萄糖共转运体 2 抑制剂作为活性成分，非常适合作为不仅是普通脂肪肝，而且是非胆汁性脂肪肝（NAFL）、非胆汁性脂肪性肝炎（NASH）、高营养脂肪肝、糖尿病脂肪肝、胆汁性脂肪肝中毒性脂肪肝或类似疾病的进展抑制剂。
• GLUCOPYRANOSYLOXYBENZYLBENZENE DERIVATIVES AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1329456B1

  公开（公告）日：2006-08-09
• METHOD FOR TREATING HYPERURICEMIA EMPLOYING AN SGLT2 INHIBITOR AND COMPOSITION CONTAINING SAME
  申请人：AstraZeneca AB

  公开号：EP2291189B1

  公开（公告）日：2014-10-01
• Progression Inhibitor For Disease Attributed To Abnormal Accumulation Of Liver Fat
  申请人：Katsuno Kenji

  公开号：US20080045466A1

  公开（公告）日：2008-02-21

  The present invention provides pharmaceutical compositions useful as agents for the inhibition of progression of diseases associated with abnormal accumulation of liver lipids. In particular, the pharmaceutical compositions of the present invention which comprise as an active ingredient a sodium/glucose co-transporter 2 inhibitor are highly suitable as an agent for the inhibition of progression of not only common fatty liver but also non-alcholic fatty liver disease (NAFL), non-alcholic steatohepatitis (NASH), hypernutritive fatty liver, diabetic fatty liver, alcholic fatty liver disease toxic fatty liver or the like.