(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol | 866605-96-1

• 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-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (3R,4S,5S,6R)-2-[3-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-chlorophenyl]-6-(hydroxymethyl)-2-methoxyoxane-3,4,5-triol
• CAS: 866605-96-1
• 化学式: C₃₀H₃₇ClO₇Si
• 分子量: 573.158
• InChiKey: HOSXHIDAYFALDJ-VAUJRCAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 17.0h， 生成 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((6-fluoro-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties

  摘要：

  The sodium glucose co-transporter 2 (SGLT2) has received considerable attention in recent years as a target for the treatment of type 2 diabetes mellitus. This report describes the design, synthesis and structure-activity relationship (SAR) of C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties as novel SGLT2 inhibitors. Compounds 5p and 33b demonstrated high potency in inhibiting SGLT2 and high selectivity against SGLT1. The in vitro ADMET properties of these compounds will also be discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.036
• 作为产物：
  描述：

  甲醇 、 (5-bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane 、 2,3,4,6-四-O-三甲基硅基-D-葡萄糖酸内酯 在 叔丁基锂 、 甲烷磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties

  摘要：

  The sodium glucose co-transporter 2 (SGLT2) has received considerable attention in recent years as a target for the treatment of type 2 diabetes mellitus. This report describes the design, synthesis and structure-activity relationship (SAR) of C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties as novel SGLT2 inhibitors. Compounds 5p and 33b demonstrated high potency in inhibiting SGLT2 and high selectivity against SGLT1. The in vitro ADMET properties of these compounds will also be discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.036

文献信息

• The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties
  作者：Cheng Guo、Min Hu、Russell J. DeOrazio、Alexander Usyatinsky、Kevin Fitzpatrick、Zhenjun Zhang、Jun-Ho Maeng、Douglas B. Kitchen、Susan Tom、Michele Luche、Yuri Khmelnitsky、Andrew J. Mhyre、Peter R. Guzzo、Shuang Liu

  DOI：10.1016/j.bmc.2014.04.036

  日期：2014.7

  The sodium glucose co-transporter 2 (SGLT2) has received considerable attention in recent years as a target for the treatment of type 2 diabetes mellitus. This report describes the design, synthesis and structure-activity relationship (SAR) of C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties as novel SGLT2 inhibitors. Compounds 5p and 33b demonstrated high potency in inhibiting SGLT2 and high selectivity against SGLT1. The in vitro ADMET properties of these compounds will also be discussed. (C) 2014 Elsevier Ltd. All rights reserved.