Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-propylsulfanyl-tetrahydro-pyran-3-yl ester | 35785-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-propylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS: 35785-57-0
• 化学式: C₁₄H₂₂O₇S
• 分子量: 334.39
• InChiKey: PVVCWYWAPGYIFZ-RQJABVFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-propylsulfanyl-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 propyl 1-S β-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
• 作为产物：
  描述：

  丙烷-1-硫醇 、 tetra-O-acetyl-β-D-xylopyranose 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-propylsulfanyl-tetrahydro-pyran-3-yl ester
  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