1,2-O-isopropylidene-3-C-phenyl-α-D-ribofuranose | 237412-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-isopropylidene-3-C-phenyl-α-D-ribofuranose
• CAS: 237412-43-0
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: RUTQGNKMWKFHDL-GFQSEFKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-C-phenyl-α-D-ribofuranose 在 4-二甲氨基吡啶 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 1,2-O-isopropylidene-3-C-phenyl-5-(4-(hydroxymethyl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases

  摘要：

  Ten new 1,2,3-triazole glycoconjugates were synthesized from D-glucose and evaluated in in vitro assays for their ability to inhibit the enzyme a-glucosidase. Most of the compounds had low activity or were inactive when compared with acarbose. However, the derivative 1,2-O-isopropylidene-3-phenyl-5-(4-phenyl- 1H-1,2,3-triazole-1-yl)-alpha-D-ribofuranose (19i) possessed activity comparable with the standard drug. The influence of the phenyl group on carbon 3 of the carbohydrate framework is discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.026
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 1,2-O-isopropylidene-3-C-phenyl-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases

  摘要：

  Ten new 1,2,3-triazole glycoconjugates were synthesized from D-glucose and evaluated in in vitro assays for their ability to inhibit the enzyme a-glucosidase. Most of the compounds had low activity or were inactive when compared with acarbose. However, the derivative 1,2-O-isopropylidene-3-phenyl-5-(4-phenyl- 1H-1,2,3-triazole-1-yl)-alpha-D-ribofuranose (19i) possessed activity comparable with the standard drug. The influence of the phenyl group on carbon 3 of the carbohydrate framework is discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.026