1-deoxy-2,3:4,5-di-O-isopropylidene-1-thiocyanato-β-D-fructopyranose | 223388-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1-deoxy-2,3:4,5-di-O-isopropylidene-1-thiocyanato-β-D-fructopyranose
• 英文别名: [(1R,2S,6R,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl thiocyanate
• CAS: 223388-76-9
• 化学式: C₁₃H₁₉NO₅S
• 分子量: 301.364
• InChiKey: KRQJEOWOTZJWNA-DNJQJEMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-deoxy-2,3:4,5-di-O-isopropylidene-1-thiocyanato-β-D-fructopyranose 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 1-thio-1-S-trifluoromethyl-β-D-fructopyranose
  参考文献：
  名称：

  An unprecedented access to trifluoromethylthiosugar derivatives from thiocyanate precursors upon treatment with trifluoromethyltrimethylsilane

  摘要：

  Upon treatment with trifluoromethyltrimethylsilane (2 equiv) in oxolane at 0 degrees C in the presence of a catalytic amount of tetra-n-butylammonium fluoride (0.2 equiv), various protected sugar derivatives having a thiocyanato group attached to different positions (anomeric, secondary, primary) were converted into the corresponding trifluoromethylthio derivatives. Under these conditions, highly selective, albeit partial transformations of primary and secondary thiocyanate groups were achieved while a decreased selectivity was observed when the reaction involved a more reactive anomeric thiocyanate group. However, in this case, lowering the reaction temperature led to enhanced selectivity and higher isolated yields. The isopropylidene and benzoyl protecting groups in the resulting trifluoromethylthiosugar derivatives were removed by standard methods to afford the corresponding free trifluoromethylthio derivatives, generally in high yield and as crystalline solids. Hence, this method opens a practical access to new trifluoromethylthiosugars obtained under smooth conditions as protected or unprotected derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00289-4
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-β-D-fructopyranose 、 potassium thioacyanate 以 乙腈 为溶剂， 反应 19.0h， 以72%的产率得到1-deoxy-2,3:4,5-di-O-isopropylidene-1-thiocyanato-β-D-fructopyranose
  参考文献：
  名称：

  An unprecedented access to trifluoromethylthiosugar derivatives from thiocyanate precursors upon treatment with trifluoromethyltrimethylsilane

  摘要：

  Upon treatment with trifluoromethyltrimethylsilane (2 equiv) in oxolane at 0 degrees C in the presence of a catalytic amount of tetra-n-butylammonium fluoride (0.2 equiv), various protected sugar derivatives having a thiocyanato group attached to different positions (anomeric, secondary, primary) were converted into the corresponding trifluoromethylthio derivatives. Under these conditions, highly selective, albeit partial transformations of primary and secondary thiocyanate groups were achieved while a decreased selectivity was observed when the reaction involved a more reactive anomeric thiocyanate group. However, in this case, lowering the reaction temperature led to enhanced selectivity and higher isolated yields. The isopropylidene and benzoyl protecting groups in the resulting trifluoromethylthiosugar derivatives were removed by standard methods to afford the corresponding free trifluoromethylthio derivatives, generally in high yield and as crystalline solids. Hence, this method opens a practical access to new trifluoromethylthiosugars obtained under smooth conditions as protected or unprotected derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00289-4