D-glucose diethyldithioacetal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glucose diethyldithioacetal
• 英文别名: (2S,3S,4R,5S)-6,6-bis(ethylsulfanyl)hexane-1,2,3,4,5-pentol
• 化学式: C₁₀H₂₂O₅S₂
• 分子量: 286.414
• InChiKey: BTOYCPDACQXQRS-MAUMQABQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.75
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101.15
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 D-glucose diethyldithioacetal 在 吡啶 作用下， 反应 19.0h， 生成 2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal
  参考文献：
  名称：

  Synthesis of peracetylated C-1-deoxyalditol- and C-glycoside-dipyrranes via dithioacetal derivatives

  摘要：

  Dipyrranes bearing peracetylated mono- or disaccharidic C-1-deoxyalditol moieties were prepared from D-galactose, c-glucose, c-mannose, and lactose. A partially hydrolyzed polysaccharide (agarose) was also used as starting material for the synthesis of a disaccharide-containing C-glycoside dipyrrane. These compounds were synthesized as follows: the sugar starting materials were first submitted to a mercaptolysis-acetylation one-pot procedure (EtSH/HCl-Ac2O/pyridine). The resulting peracetylated diethyl dithioacetals were converted into dipyrranes through carbonyl deprotection (H5IO6, THF-Et2O) followed by TFA-catalyzed pyrrole condensation with yields up to 62%. Overall yields from sugar starting materials were up to 49%. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.12.048
• 作为产物：
  描述：

  D-葡萄糖 、 乙硫醇 在 盐酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 D-glucose diethyldithioacetal
  参考文献：
  名称：

  Synthesis of peracetylated C-1-deoxyalditol- and C-glycoside-dipyrranes via dithioacetal derivatives

  摘要：

  Dipyrranes bearing peracetylated mono- or disaccharidic C-1-deoxyalditol moieties were prepared from D-galactose, c-glucose, c-mannose, and lactose. A partially hydrolyzed polysaccharide (agarose) was also used as starting material for the synthesis of a disaccharide-containing C-glycoside dipyrrane. These compounds were synthesized as follows: the sugar starting materials were first submitted to a mercaptolysis-acetylation one-pot procedure (EtSH/HCl-Ac2O/pyridine). The resulting peracetylated diethyl dithioacetals were converted into dipyrranes through carbonyl deprotection (H5IO6, THF-Et2O) followed by TFA-catalyzed pyrrole condensation with yields up to 62%. Overall yields from sugar starting materials were up to 49%. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.12.048

文献信息

• Bingham, Steve J.; Tyman, John H. P.; Malik, K. M. A., Journal of Chemical Research, Miniprint, 1998, # 9, p. 2465 - 2496
  作者：Bingham, Steve J.、Tyman, John H. P.、Malik, K. M. A.、Hibbs, David E.、Hursthouse, Michael B.

  DOI：——

  日期：——
• Synthesis of peracetylated C-1-deoxyalditol- and C-glycoside-dipyrranes via dithioacetal derivatives
  作者：Stephanie M.S. Ló、Juliana C. Cunico、Diogo R.B. Ducatti、Alexandre Orsato、M. Eugênia R. Duarte、Sandra M.W. Barreira、Miguel D. Noseda、Alan G. Gonçalves

  DOI：10.1016/j.tetlet.2012.12.048

  日期：2013.2

  Dipyrranes bearing peracetylated mono- or disaccharidic C-1-deoxyalditol moieties were prepared from D-galactose, c-glucose, c-mannose, and lactose. A partially hydrolyzed polysaccharide (agarose) was also used as starting material for the synthesis of a disaccharide-containing C-glycoside dipyrrane. These compounds were synthesized as follows: the sugar starting materials were first submitted to a mercaptolysis-acetylation one-pot procedure (EtSH/HCl-Ac2O/pyridine). The resulting peracetylated diethyl dithioacetals were converted into dipyrranes through carbonyl deprotection (H5IO6, THF-Et2O) followed by TFA-catalyzed pyrrole condensation with yields up to 62%. Overall yields from sugar starting materials were up to 49%. (C) 2012 Published by Elsevier Ltd.