(3S,4R,5R,6R)-2-[5-(bromomethyl)-4-chloro-2-methoxyphenyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane | 1313512-94-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5R,6R)-2-[5-(bromomethyl)-4-chloro-2-methoxyphenyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1313512-94-5
• 化学式: C₄₂H₄₂BrClO₆
• 分子量: 758.149
• InChiKey: JEXBTZPGAIFVII-GLTXCYADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6R)-2-[5-(bromomethyl)-4-chloro-2-methoxyphenyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane 在 18-冠醚-6 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 16.0h， 生成 2-(2-chloro-4-methoxy-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)acetic acid
  参考文献：
  名称：

  Thiazolylmethyl ortho-substituted phenyl glucoside library as novel C-aryl glucoside SGLT2 inhibitors

  摘要：

  In order to investigate SAR regarding proximal phenyl ring in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on proximal phenyl ring was conducted. During a series of lead optimization efforts, ortho-allyloxyphenyl 10p or ortho-hydroxyphenyl ha showed subnanomolar inhibitory activity against hSGLT2. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.052
• 作为产物：
  描述：

  2-氯-4-羟基苯甲腈 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 lithium hydroxide monohydrate 、 三氟甲磺酸 、 dimethyl sulfide borane 、 四丁基氟化铵 、 三溴化磷 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.0h， 生成 (3S,4R,5R,6R)-2-[5-(bromomethyl)-4-chloro-2-methoxyphenyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
  参考文献：
  名称：

  Thiazolylmethyl ortho-substituted phenyl glucoside library as novel C-aryl glucoside SGLT2 inhibitors

  摘要：

  In order to investigate SAR regarding proximal phenyl ring in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on proximal phenyl ring was conducted. During a series of lead optimization efforts, ortho-allyloxyphenyl 10p or ortho-hydroxyphenyl ha showed subnanomolar inhibitory activity against hSGLT2. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.052

文献信息

• Thiazolylmethyl ortho-substituted phenyl glucoside library as novel C-aryl glucoside SGLT2 inhibitors
  作者：Suk Ho Lee、Min Ju Kim、Sung-Han Lee、Jeongmin Kim、Hyun-Ju Park、Jinhwa Lee

  DOI：10.1016/j.ejmech.2011.03.052

  日期：2011.7

  In order to investigate SAR regarding proximal phenyl ring in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on proximal phenyl ring was conducted. During a series of lead optimization efforts, ortho-allyloxyphenyl 10p or ortho-hydroxyphenyl ha showed subnanomolar inhibitory activity against hSGLT2. (C) 2011 Elsevier Masson SAS. All rights reserved.