1-O-methyl-2,3,4-O-pivaloyl-β-D-xylopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-methyl-2,3,4-O-pivaloyl-β-D-xylopyranoside
• 英文别名: Methyl 2,3,4-tri-O-pivaloyl-beta-D-xylopyranoside；[(3R,4S,5R,6R)-4,5-bis(2,2-dimethylpropanoyloxy)-6-methoxyoxan-3-yl] 2,2-dimethylpropanoate
• 化学式: C₂₁H₃₆O₈
• 分子量: 416.512
• InChiKey: AQNSTZWJYAPYIK-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  三甲基乙酰氯 、 甲基-β-D-吡喃木糖苷 在 吡啶 作用下， 反应 24.0h， 以90%的产率得到1-O-methyl-2,3,4-O-pivaloyl-β-D-xylopyranoside
  参考文献：
  名称：

  兔血清酯酶的酰化甲基-β-d-吡喃吡喃糖苷的合成及其酶促脱酰作用

  摘要：

  已经在各种反应条件下研究了甲基β-D-吡喃吡喃糖苷的选择性Pivaloylations。部分聚乙烯醇化的产物需要进行额外的乙酰化。通过1H NMR光谱确定结构。酰化的甲基β-D-吡喃吡喃糖苷（酰基为新戊酰，乙酰基或两者的组合）的代表通过兔血清和从兔血清中分离出的酯酶催化水解。

  DOI：

  10.1016/s0008-6215(97)00104-3

文献信息

• Synthesis of acylated methyl -β-d-xylopyranosides and their enzymic deacylations by rabbit serum esterases
  作者：Vesna Petrović、Srdanka Tomić、Durdica Ljevaković、Jelka Tomasˇić

  DOI：10.1016/s0008-6215(97)00104-3

  日期：1997.7

  Selective pivaloylations of methyl beta-D-xylopyranoside have been studied under various reaction conditions. Partially pivaloylated products were submitted to additional acetylations. The structures were established by 1H NMR spectroscopy. Representatives of acylated methyl beta-D-xylopyranosides (acyl being pivaloyl, acetyl, or a combination of both) were submitted to hydrolysis catalyzed by rabbit

  已经在各种反应条件下研究了甲基β-D-吡喃吡喃糖苷的选择性Pivaloylations。部分聚乙烯醇化的产物需要进行额外的乙酰化。通过1H NMR光谱确定结构。酰化的甲基β-D-吡喃吡喃糖苷（酰基为新戊酰，乙酰基或两者的组合）的代表通过兔血清和从兔血清中分离出的酯酶催化水解。
• Novel <scp>d</scp>-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α
  作者：Arie Gruzman、Ofer Shamni、Moriya Ben Yakir、Daphna Sandovski、Anna Elgart、Evgenia Alpert、Guy Cohen、Amnon Hoffman、Yehoshua Katzhendler、Erol Cerasi、Shlomo Sasson

  DOI：10.1021/jm8008713

  日期：2008.12.25

  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.