1-azido-1-deoxy-D-gluco-hept-2-ulopyranose | 137041-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-azido-1-deoxy-D-gluco-hept-2-ulopyranose
• 英文别名: (2S,3R,4S,5S,6R)-2-(azidomethyl)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• CAS: 137041-91-9
• 化学式: C₇H₁₃N₃O₆
• 分子量: 235.197
• InChiKey: MYDFQZHHEDPHMV-ZFYZTMLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-azido-1-deoxy-D-gluco-hept-2-ulopyranose 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到1-amino-1-deoxy-D-gluco-hept-2-ulopyranose
  参考文献：
  名称：

  A new approach to Amadori ketoses via MoVI-catalyzed stereospecific isomerization of 2-C-branched sugars bearing azido function in a microwave field

  摘要：

  A branched-chain aldose bearing an azido group at the C-2 position provides access to the corresponding 1-deoxy-1-azido- and 1-deoxy-1-amino ketoses in a single step via stereospecific isomerization. The isomerization exploited the catalytic effect of molybdate ions and microwave irradiation. The structures of the products were analyzed by NMR spectroscopy, IR, HRMS spectrometry and quantum-chemical DFT calculations. DFT-computed proton-proton coupling constants of the prepared Amadori ketose 1-deoxy1-amino-D-gluco-heptulose were found to be comparable with the experimentally obtained coupling constants and were in agreement with the C-4(1) pyranose form in aqueous solution at room temperature. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.027
• 作为产物：
  描述：

  2-C-(azidomethyl)-2-deoxy-D-mannopyranose 在 水 、 molybdic acid 作用下， 反应 0.17h， 以98%的产率得到1-azido-1-deoxy-D-gluco-hept-2-ulopyranose
  参考文献：
  名称：

  A new approach to Amadori ketoses via MoVI-catalyzed stereospecific isomerization of 2-C-branched sugars bearing azido function in a microwave field

  摘要：

  A branched-chain aldose bearing an azido group at the C-2 position provides access to the corresponding 1-deoxy-1-azido- and 1-deoxy-1-amino ketoses in a single step via stereospecific isomerization. The isomerization exploited the catalytic effect of molybdate ions and microwave irradiation. The structures of the products were analyzed by NMR spectroscopy, IR, HRMS spectrometry and quantum-chemical DFT calculations. DFT-computed proton-proton coupling constants of the prepared Amadori ketose 1-deoxy1-amino-D-gluco-heptulose were found to be comparable with the experimentally obtained coupling constants and were in agreement with the C-4(1) pyranose form in aqueous solution at room temperature. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.027