改进的Williamson醚化法合成葡萄糖衍生物

An Improved Williamson Etherification Method for Synthesis of Glucose Derivatives

以葡萄糖衍生物、碱金属氢氧化物、氯化苄为原料,以正辛烷为带水剂,经Williamson醚化反应合成了3个苄醚化葡萄糖衍生物。考察了带水剂、碱、苄醚化试剂及投料比对反应的影响,得到优化的反应条件为:n(底物羟基)∶n(氢氧化钾或氢氧化钠)∶n(氯化苄)=1.00∶(1.10~1.15)∶(1.10~1.15),正辛烷为带水剂,125~130℃保温回流脱水反应4 h,在该条件下产物产率为96.8%~98.2%。产物结构经FTIR、UPLC-MASS、1HNMR确证。

Three benzylated glucose derivatives were synthesized via an improved Williamson etherification method using glucose derivatives,alkali metal hydroxide and benzyl chloride as raw material,n-octane as water-carrying agent.The kind of water-carrying agent,the kind of alkali metal hydroxide,the kind of benzyl-etherification agent,and the mole ratio of raw material were selected to investigate their influence on the yield of the benzylated glucose derivatives.The optimum synthesis conditions were obtained.When the mole ratio of hydroxy of substrate,KOH or Na OH,and benzyl chloride was 1.00 ∶（1.10 - 1.15） ∶（1.10 - 1.15）,using n-octane as water-carrying agent,and the reaction refluxed at 125 - 130 ℃ for 4 h,three benzylated glucose derivatives showed high yields of96.8% - 98.2%.These compounds were characterized by FTIR,HPLC- MASS,and1 HNMR.