3-phenyl-1-(2,4,6-tris(benzyloxy)-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)prop-2-en-1-one | 1266170-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-phenyl-1-(2,4,6-tris(benzyloxy)-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)prop-2-en-1-one
• CAS: 1266170-02-8
• 化学式: C₄₂H₄₀O₉
• 分子量: 688.774
• InChiKey: YYKRPKWHXALPBC-CFOUBNKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  134.91
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(2,4,6-tris(benzyloxy)-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)prop-2-en-1-one 在 10% palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 生成 1-[3-(β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-3-phenylpropan-1-one
  参考文献：
  名称：

  Synthesis and antihyperglycemic activity of phenolic C-glycosides

  摘要：

  Various phenolic C-glycosides were evaluated for their in vitro and in vivo antihyperglycemic activity employing glucose uptake by rat muscle cell lines (L-6) and low dosed-streptozotocin-induced diabetic rats, respectively. Some of phenolic C-glycosides were isolated from Pterocarpus marsupium and Ulmus wallichiana and other were synthesized by unprotected sugar and phloroacetophenone using Sc(OTf)(3) in aqueous ethanol. Eight among tested compounds showed significant lowering of blood glucose level on low dosed-streptozotocin-induced diabetic rats. The compound 24 lowered the blood glucose levels by 34.9% and 33.6% during 0-5 h and 0-24 h, respectively, at the dose of 25 mg/kg body weight which is comparable to standard antidiabetic drug metformin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.031
• 作为产物：
  描述：

  1-(2,4,6-tris(benzyloxy)-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)ethan-1-one 、 苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-phenyl-1-(2,4,6-tris(benzyloxy)-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and antihyperglycemic activity of phenolic C-glycosides

  摘要：

  Various phenolic C-glycosides were evaluated for their in vitro and in vivo antihyperglycemic activity employing glucose uptake by rat muscle cell lines (L-6) and low dosed-streptozotocin-induced diabetic rats, respectively. Some of phenolic C-glycosides were isolated from Pterocarpus marsupium and Ulmus wallichiana and other were synthesized by unprotected sugar and phloroacetophenone using Sc(OTf)(3) in aqueous ethanol. Eight among tested compounds showed significant lowering of blood glucose level on low dosed-streptozotocin-induced diabetic rats. The compound 24 lowered the blood glucose levels by 34.9% and 33.6% during 0-5 h and 0-24 h, respectively, at the dose of 25 mg/kg body weight which is comparable to standard antidiabetic drug metformin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.031