methyl (2S,3S)-2,3-dihydroxy-3-(5-methylfuran-2-yl)propanoate | 1266556-01-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2S,3S)-2,3-dihydroxy-3-(5-methylfuran-2-yl)propanoate
• CAS: 1266556-01-7
• 化学式: C₉H₁₂O₅
• 分子量: 200.191
• InChiKey: ONRORMVHIAOEMJ-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-2,3-dihydroxy-3-(5-methylfuran-2-yl)propanoate 在 氧气 、 rose bengal 、 二甲基硫 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 以75%的产率得到methyl (1S,5R,7S)-5-methyl-2-oxo-6,8-dioxabicyclo[3.2.1]oct-3-ene-7-carboxylate
  参考文献：
  名称：

  Scope and Limitations of the Photooxidations of 2-(α-Hydroxyalkyl)furans: Synthesis of 2-Hydroxy-exo-brevicomin

  摘要：

  Photooxygenation of 2-(alpha-hydroxyalkyl)furans at 5 degrees C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(alpha,beta-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.

  DOI：

  10.1021/ol200027f
• 作为产物：
  描述：

  methyl 3-(5-methyl-2-furyl)acrylate 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 以78%的产率得到methyl (2S,3S)-2,3-dihydroxy-3-(5-methylfuran-2-yl)propanoate
  参考文献：
  名称：

  Scope and Limitations of the Photooxidations of 2-(α-Hydroxyalkyl)furans: Synthesis of 2-Hydroxy-exo-brevicomin

  摘要：

  Photooxygenation of 2-(alpha-hydroxyalkyl)furans at 5 degrees C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(alpha,beta-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.

  DOI：

  10.1021/ol200027f

文献信息

• Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds
  作者：Dimitris Noutsias、Ioanna Alexopoulou、Tamsyn Montagnon、Georgios Vassilikogiannakis

  DOI：10.1039/c2gc16397g

  日期：——

  A new set of completely green methods utilising air, light, water and spirulina to transform readily accessible furan substrates into a diverse range of synthetically useful polyoxygenated motifs commonly found in natural products is presented herein.

  本文介绍了一套全新的绿色方法，利用空气、光、水和螺旋藻将易获得的呋喃底物转化为在天然产物中常见的多种合成上有用的多氧官能团结构单元。
• Scope and Limitations of the Photooxidations of 2-(α-Hydroxyalkyl)furans: Synthesis of 2-Hydroxy-<i>exo</i>-brevicomin
  作者：Dimitris Noutsias、Antonia Kouridaki、Georgios Vassilikogiannakis

  DOI：10.1021/ol200027f

  日期：2011.3.4

  Photooxygenation of 2-(alpha-hydroxyalkyl)furans at 5 degrees C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(alpha,beta-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.