4-aminomethyltriazol-1-yl 2,3-O-isopropylidene-β-D-ribofuranoside | 1474027-17-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 4-aminomethyltriazol-1-yl 2,3-O-isopropylidene-β-D-ribofuranoside
• 英文别名: [(3aR,4R,6R,6aR)-4-[4-(aminomethyl)triazol-1-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 1474027-17-2
• 化学式: C₁₁H₁₈N₄O₄
• 分子量: 270.288
• InChiKey: XNTSJUIQWZGEMS-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  β-D-Ribofuranosylazid 在 高氯酸 、 copper acetate monohydrate 、 sodium carbonate 、 sodium ascorbate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 4-aminomethyltriazol-1-yl 2,3-O-isopropylidene-β-D-ribofuranoside
  参考文献：
  名称：

  Efficient Synthesis of a Water-Soluble Glucoamide Inhibitor Against Human Aldose Reductase by Click Chemistry

  摘要：

  While D-glucose is the natural substrate of aldose reductase (AR) in the polyol pathway, the K-m value of D-glucose against AR is large. A glucoamide 1 was designed as a tool to investigate whether AR has a strong affinity for the open form of D-glucose. Glucoamide 1 was synthesized in high yield by modification of the reaction condition for click chemistry. It was found that our modified condition was applicable for highly polar alkynes and gave coupling products in excellent yield (90% to 100%). Although weak inhibitory activity against AR was observed, kinetic studies showed that AR does not accept glucoamide 1 in its active site.

  DOI：

  10.1080/07328303.2013.816852

文献信息

• Efficient Synthesis of a Water-Soluble Glucoamide Inhibitor Against Human Aldose Reductase by Click Chemistry
  作者：Mikio Fujii、Shinji Sudo、Yasuyuki Kitagawa、Keisuke Kato

  DOI：10.1080/07328303.2013.816852

  日期：2013.9.2

  While D-glucose is the natural substrate of aldose reductase (AR) in the polyol pathway, the K-m value of D-glucose against AR is large. A glucoamide 1 was designed as a tool to investigate whether AR has a strong affinity for the open form of D-glucose. Glucoamide 1 was synthesized in high yield by modification of the reaction condition for click chemistry. It was found that our modified condition was applicable for highly polar alkynes and gave coupling products in excellent yield (90% to 100%). Although weak inhibitory activity against AR was observed, kinetic studies showed that AR does not accept glucoamide 1 in its active site.