(R)-1-((2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-2-yl)prop-2-en-1-ol | 1270018-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-2-yl)prop-2-en-1-ol
• CAS: 1270018-04-6
• 化学式: C₄₃H₄₀ClNO₆S
• 分子量: 734.313
• InChiKey: XKCKKRKASMURKT-VFEPHYMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.39
• 重原子数：
  52.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.18
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-2-yl)prop-2-en-1-ol 在 三氯化硼 作用下， 生成 (2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-6-(1-hydroxyallyl)-tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Exploration of SAR regarding glucose moiety in novel C-aryl glucoside inhibitors of SGLT2

  摘要：

  In order to investigate SAR regarding glucose moiety in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on glucose was conducted to explore potential utility as a suitable replacement of glucose per se. Among the compounds prepared, deshydroxy 29 (IC50 = 7.01 nM) demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date. But, none of the compounds were better than the parent molecule 5 (IC50 = 1.75 nM). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.115
• 作为产物：
  描述：

  2-[[2-chloro-5-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]phenyl]methyl]-5-(furan-2-yl)-1,3-thiazole 在 三氟甲磺酸三甲基硅酯 、 乙酸酐 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (R)-1-((2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-2-yl)prop-2-en-1-ol
  参考文献：
  名称：

  Exploration of SAR regarding glucose moiety in novel C-aryl glucoside inhibitors of SGLT2

  摘要：

  In order to investigate SAR regarding glucose moiety in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on glucose was conducted to explore potential utility as a suitable replacement of glucose per se. Among the compounds prepared, deshydroxy 29 (IC50 = 7.01 nM) demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date. But, none of the compounds were better than the parent molecule 5 (IC50 = 1.75 nM). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.115