2,3,4-tri-O-acetyl-D-arabinopyranose | 10369-25-2

• 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: 2,3,4-tri-O-acetyl-D-arabinopyranose
• 英文别名: O²,O³,O⁴-Triacetyl-β-D-arabinopyranose；[(3R,4R,5S,6R)-4,5-diacetyloxy-6-hydroxyoxan-3-yl] acetate
• CAS: 10369-25-2；70135-47-6；86032-22-6；86032-23-7；101857-06-1；106820-14-8；120019-52-5
• 化学式: C₁₁H₁₆O₈
• 分子量: 276.243
• InChiKey: NHLHTUYICZOCMA-CHWFTXMASA-N

物化性质

• 沸点：
  351.5±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  benzyl-(tri-O-acetyl-β-D-arabinopyranoside) 在 palladium on activated charcoal 、 乙醚 作用下， 生成 2,3,4-tri-O-acetyl-D-arabinopyranose
  参考文献：
  名称：

  Reductive Cleavage of Benzyl Glycosides for Relating Anomeric Configurations. Preparation of Some New Benzyl Pentosides¹

  摘要：

  DOI：

  10.1021/ja01147a076

文献信息

• Leuckart–Wallach Approach to Sugar Isocyanides and Its IMCRs
  作者：Alexander Dömling、Constantinos Neochoritis、Ji Zhang

  DOI：10.1055/s-0034-1381046

  日期：——

  We utilize our recently introduced Leuckart-Wallach approach to synthesize anomeric sugar isocyanides in good overall yields and two steps. Moreover, we show the general usage of these isocyanides in isocyanide-based multicomponent reactions (IMCRs) to produce eight different compounds/scaffolds.
• A highly efficient deprotection of the 2,2,2-trichloroethyl group at the anomeric oxygen of carbohydrates
  作者：Jianbo Zhang、Jie Fu、Wenshuai Si、Xiaohu Wang、Zhongfu Wang、Jie Tang

  DOI：10.1016/j.carres.2011.08.007

  日期：2011.8

  Commercially available zinc dust in the presence of ammonium chloride in acetonitrile at reflux removes the 2,2,2-trichloroethyl (ICE) group at anomeric centers with excellent yields (>95%) in short reaction times. This present method is easily implemented on substrates containing acyl and benzyl groups and large-scale reactions also proceed in high yield. (C) 2011 Elsevier Ltd. All rights reserved.