D-fructose diethyl dithioacetal | 148979-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-fructose diethyl dithioacetal
• 英文别名: D-fructose-diethyldithioacetal；D-arabino-1,3,4,5,6-Pentahydroxy-hexan-2-on-diaethyldithioacetal；D-lyxo-5,5-Bis-aethylmercapto-hexan-1,2,3,4,6-pentaol；D-Fructose-diaethyldithioacetal
• CAS: 148979-53-7
• 化学式: C₁₀H₂₂O₅S₂
• 分子量: 286.414
• InChiKey: PZKHHNKSRQMRSN-HLTSFMKQSA-N

物化性质

• 沸点：
  570.3±50.0 °C(predicted)
• 密度：
  1.362±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.74
• 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：

  D-fructose diethyl dithioacetal 在 氨 、 水 、 碘 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 mercury dichloride 、 mercury(II) oxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.5h， 生成 2-Deoxy-D-glucose
  参考文献：
  名称：

  Photolysis of 2-azi-2-deoxy-d-arabino-hexitol and analogous hexitols; the ineffectiveness of certain carbohydrate diazirines as photoaffinity labels

  摘要：

  Three diazirines 2-azi-2-deoxy-D-arabino-hexitol (4), its 1-deoxy analogue (5), and 3-azi-3,6-dideoxy-L-xylo-hexitol (9) were synthesised and their products of photolysis analysed by TLC. Diazirine 4 gave exclusively 2-deoxy-D-arabino-hexose (12), 5 gave predominantly 1,2-dideoxy-D-erythro-3-hexulose (10) and 1-deoxy-D-glucitol (11), and 9 did not yield any main product. Carrying out the irradiation of 4 in D2O gave selectively (2S)-2-deoxy-D-arabino-(2-H-2)hexose (12a). The results indicate that photolysis of a diazirine flanked by a hydroxymethyl group, as in compound 4, leads to a rapid and stereoselective intramolecular reaction of the intermediate. This may be an explanation of why compound 4 is ineffective as a photoaffinity reagent for mannitol permease (D-mannitol-specific enzyme II) of the E. coli phosphotransferase system for which it is a substrate. A secondary hydroxymethylene group has a less pronounced effect and still allows some reaction with the medium.

  DOI：

  10.1016/0008-6215(93)84209-o
• 作为产物：
  描述：

  1,3,4,5,6-penta-O-acetyl-keto-D-fructose 在 甲醇 、 氨 、 sodium sulfate 、 zinc(II) chloride 作用下， 生成 D-fructose diethyl dithioacetal
  参考文献：
  名称：

  Keto-Fructose Pentaacetate

  摘要：

  DOI：

  10.1021/ja01319a034

文献信息

• Glycofuranosides and Thioglycofuranosides. VI. Preparation of Dimethyl Acetal and Methylfuranosides from <i>d</i>-Fructosediethylmercaptal
  作者：Eugene. Pacsu

  DOI：10.1021/ja01876a011

  日期：1939.7
• Bredereck et al., Chemische Berichte, 1953, vol. 86, p. 476,481
  作者：Bredereck et al.

  DOI：——

  日期：——