2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose diethyl dithioacetal | 160849-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose diethyl dithioacetal
• 英文别名: 2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose diethyl-dithioacetal
• CAS: 160849-24-1
• 化学式: C₂₆H₃₆O₄S₂
• 分子量: 476.701
• InChiKey: JQGVLICMOPBXKC-WXFUMESZSA-N

物化性质

• 沸点：
  594.261±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.126±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  32.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose diethyl dithioacetal 在 过氧乙酸 、 三氟化硼乙醚 、 sodium acetate 、 溶剂黄146 、 potassium bromide 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 23.5h， 生成 2,5-anhydro-3,4-di-O-benzyl-D-altritol
  参考文献：
  名称：

  Preparation of 2,5-Anhydrohexitols (Part I). Silicon-Directed Stereocontrolled Cyclization

  摘要：

  Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3. Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.

  DOI：

  10.1080/07328309908543989
• 作为产物：
  描述：

  D-ribose diethyl dithioacetal 在 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose diethyl dithioacetal
  参考文献：
  名称：

  Preparation of 2,5-Anhydrohexitols (Part I). Silicon-Directed Stereocontrolled Cyclization

  摘要：

  Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3. Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.

  DOI：

  10.1080/07328309908543989

文献信息

• Cycloaddition reactions of carbohydrate derivatives. Part V. A hetero Diels-Alder approach to swainsonine analogs
  作者：Pál Herczegh、Imre Kovács、László Szilágyi、Ferenc Sztaricskai、Amaya Berecibar、Claude Riche、Angèle Chiaroni、Alain Olesker、Gabor Lukacs

  DOI：10.1016/s0040-4020(01)85680-5

  日期：1994.1

  Diastereoselective hetero Diels-Alder reactions of sugar derived azomethines 4a–4g have been used for the construction of chiral piperidones 6 and 7. Configuration of the major products was 6,1′-threo in every case. The enone system of 6 and 7 was reduced diastereoselectively and subsequently swainsonine-analog hydroxyindolizidines 28–32 were prepared by an intramolecular reductive amination.

  糖衍生的偶氮甲碱4a-4g的非对映选择性杂Diels-Alder反应已用于构建手性哌啶酮6和7。在每种情况下，主要产品的构型均为6,1'-苏式。非对映选择性还原6和7的烯酮体系，随后通过分子内还原胺化制备swainsonine-analog hydroxyindolizidines 28-32。