2,3,4,5,6-penta-O-acetyl-D-glucose diethyl acetal | 34370-97-3

• 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: 2,3,4,5,6-penta-O-acetyl-D-glucose diethyl acetal
• CAS: 34370-97-3
• 化学式: C₂₀H₃₂O₁₂
• 分子量: 464.467
• InChiKey: RWNZEIPYAQKGSN-AKHDSKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3,4,5,6-penta-O-acetyl-D-glucose diethyl acetal 在 Dowex 50-X₂ 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 25.5h， 生成 1,1,2,3,4,5,6-hepta-O-acetylaldehydo-D-glucose aldehydrol
  参考文献：
  名称：

  Sulfuric acid-catalyzed acetolysis of anomeric ethyl 2,3,4,6-tetra-O-acetyl-d-glucopyranosides: kinetics and mechanism

  摘要：

  Kinetics of the acetolysis and concomitant anomerization of ethyl 2,3,4,6-tetra-O-acetyl-alpha- and -beta-D-glucopyranosides in a mixture of acetic anhydride, acetic acid, and sulfuric acid have been studied. The progress of the reactions was followed by gas chromatography, and the rate constants of the partial reactions were calculated on the basis of the time-dependent product distributions obtained. The mechanisms of the reactions are discussed.

  DOI：

  10.1016/0008-6215(95)00271-5
• 作为产物：
  描述：

  乙醇 、 2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal 在 1,3-二溴-5,5-二甲基海因 作用下， 反应 0.67h， 以85%的产率得到2,3,4,5,6-penta-O-acetyl-D-glucose diethyl acetal
  参考文献：
  名称：

  Facile exchange of glycosyl S,S-acetals to their O,O-acetals and preparation of glycofuranosides from acyclic glycosyl S,S-acetals under metal-free reaction conditions in the presence of 1,3-dibromo-5,5-dimethylhydantoin

  摘要：

  Exchange of acyclic glycosyl dithioacetals to their O,O-acetals has been achieved by a generalized reaction protocol mediated by 1,3-dibromo-5,5-dimethylhydantoin under mild, metal-free and neutral conditions. This methodology has been extended to the synthesis of alkyl glycofuranosides. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.12.002