1,4-O-dimethyl-2,3-isopropylidene-α-D-xylopyranoside | 1094541-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-O-dimethyl-2,3-isopropylidene-α-D-xylopyranoside
• CAS: 1094541-31-7
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: PAAUKRMJPGRRBO-XAVMHZPKSA-N

反应信息

• 作为反应物：
  描述：

  1,4-O-dimethyl-2,3-isopropylidene-α-D-xylopyranoside 在 硫酸 作用下， 以 水 、 溶剂黄146 为溶剂， 以77.1%的产率得到4-O-methyl-α,β-D-xylopyranose
  参考文献：
  名称：

  Novel d-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α

  摘要：

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.

  DOI：

  10.1021/jm8008713
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-α-D-xylopyranoside 、 碘甲烷 在 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 以34.7%的产率得到1,4-O-dimethyl-2,3-isopropylidene-α-D-xylopyranoside
  参考文献：
  名称：

  Novel d-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α

  摘要：

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.

  DOI：

  10.1021/jm8008713