1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-2-(1H-pyrrol-1-yl)-β-D-glucopyranose | 1158974-78-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-2-(1H-pyrrol-1-yl)-β-D-glucopyranose
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-(pyrrol-1-yl)-2-deoxy-β-D-glucopyranose；1,3,4,6-tetra-O-acetyl-2-deoxy-2-(pyrrol-1-yl)-β-D-glucopyranose；[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-pyrrol-1-yloxan-2-yl]methyl acetate
• CAS: 1158974-78-7
• 化学式: C₁₈H₂₃NO₉
• 分子量: 397.382
• InChiKey: BWJFBVNEZPSSOH-DUQPFJRNSA-N

物化性质

• 沸点：
  492.7±45.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-2-(1H-pyrrol-1-yl)-β-D-glucopyranose 在 四丁基高氯酸铵 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Experimental and Theoretical Evidence of a Persistent Radical-Cation Dimer Generated during the Electrooxidation of an N-Glucosamine-pyrrole Derivative

  摘要：

  The results of the electrochemical characterization by cyclic voltammetry of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-2-(pyrro-1-yl)-beta-D-glucopyranose (Py-GSATA) are presented. This compound was analyzed in acetonitrile containing 0.1 M tetrabutylammonium perchlorate, using a platinum disk electrode as the working electrode. Py-GSATA showed two irreversible oxidation signals, the first at 1.24 and the second at 1,54 V vs Fc(+)/Fc. After successive cyclic voltammetry, under different experimental conditions, it was shown that it is not possible to electropolymerize this pyrrole derivative. Surprisingly, the bulk anodic electrolysis of Py-GSATA generated a single electroactive soluble product with an electrochemical cathodic signal located at -0.35 V vs Fc(+)/Fc. Mass spectrometry of the solution showed the presence of a dimeric species of the parent compound. ESR spectroscopy of the electrolysis solution showed a persistent radical species stable at least for 6 months (4 degrees C). UV-vis spectroscopy was consistent with low chain cation-radical oligomers. In order to propose an explanation to the dimer cation stability in solution, molecular modeling using a B3LYP/6-31+G** level of theory was used to analyze the stability and feasibility of the electrogenerated species.

  DOI：

  10.1021/jo101288j
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 以 水 、 1,2-二氯乙烷 为溶剂， 反应 0.75h， 以65%的产率得到1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-2-(1H-pyrrol-1-yl)-β-D-glucopyranose
  参考文献：
  名称：

  新型光学活性d-氨基葡萄糖-吡咯衍生物的合成

  摘要：

  由d-葡萄糖胺盐酸盐首次合成了三种新的d-葡萄糖胺-吡咯的光学活性衍生物，其吡咯基在2-和5-位未被取代。新Ñ -benzylpyrrole- d还从同一衬底制备葡糖胺衍生物。 苷-杂环-吡咯-手- d -葡

  DOI：

  10.1055/s-0028-1087968

文献信息

• Synthesis of New Optically Active <scp>d</scp>-Glucosamine-Pyrrole Derivatives
  作者：Bernardo Frontana-Uribe、Martha Escárcega-Bobadilla、Jorge Juárez-Lagunas、Rubén Toscano、Gustavo García de la Mora、Manuel Salmón

  DOI：10.1055/s-0028-1087968

  日期：——

  From d-glucosamine hydrochloride was synthesized, for the first time, three new optically active derivatives of d-glucosamine-pyrrole with the pyrrole group unsubstituted in the 2- and 5-positions. New N-benzylpyrrole-d-glucosamine derivatives were also prepared from the same substrate. glycosides - heterocycles - pyrroles - chirality - d-glucosamine

  由d-葡萄糖胺盐酸盐首次合成了三种新的d-葡萄糖胺-吡咯的光学活性衍生物，其吡咯基在2-和5-位未被取代。新Ñ -benzylpyrrole- d还从同一衬底制备葡糖胺衍生物。 苷-杂环-吡咯-手- d -葡
• Experimental and Theoretical Evidence of a Persistent Radical-Cation Dimer Generated during the Electrooxidation of an <i>N</i>-Glucosamine-pyrrole Derivative
  作者：Ulises Páramo-García、Bernardo A. Frontana-Uribe、Patricia Guadarrama、Victor M. Ugalde-Saldívar

  DOI：10.1021/jo101288j

  日期：2010.11.5

  The results of the electrochemical characterization by cyclic voltammetry of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-2-(pyrro-1-yl)-beta-D-glucopyranose (Py-GSATA) are presented. This compound was analyzed in acetonitrile containing 0.1 M tetrabutylammonium perchlorate, using a platinum disk electrode as the working electrode. Py-GSATA showed two irreversible oxidation signals, the first at 1.24 and the second at 1,54 V vs Fc(+)/Fc. After successive cyclic voltammetry, under different experimental conditions, it was shown that it is not possible to electropolymerize this pyrrole derivative. Surprisingly, the bulk anodic electrolysis of Py-GSATA generated a single electroactive soluble product with an electrochemical cathodic signal located at -0.35 V vs Fc(+)/Fc. Mass spectrometry of the solution showed the presence of a dimeric species of the parent compound. ESR spectroscopy of the electrolysis solution showed a persistent radical species stable at least for 6 months (4 degrees C). UV-vis spectroscopy was consistent with low chain cation-radical oligomers. In order to propose an explanation to the dimer cation stability in solution, molecular modeling using a B3LYP/6-31+G** level of theory was used to analyze the stability and feasibility of the electrogenerated species.