2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基异硫氰酸酯的合成与应用  

Synthesis and Application of 2,3,4,6-Tetra-O-acetyl-β-D-glycosylIsothiocyanate

作　　者：邓小娟[1] 万谦宏[1] 

机构地区：[1]天津大学药学院,天津300072

出　　处：《精细化工》2005年第4期307-310,共4页Fine Chemicals

摘　　要：以α D 葡萄糖为原料经过乙酰化、溴化、硫氰酸化三步反应合成了 2, 3, 4, 6 四 O 乙酰基 β D 吡喃葡萄糖基异硫氰酸酯。用NMR对其进行了表征。考察了相转移催化剂种类及用量、反应时间、溶剂对反应的影响。得出最佳反应条件为:以苯做溶剂,物料摩尔比为n(2, 3, 4, 6 四 O 乙酰基 α D 吡喃溴代葡萄糖)∶n(硫氰酸钾 )∶n(三乙基苄基氯化铵) =1∶2∶1,反应时间为 14h。把它用作柱前衍生试剂拆分异构体,测定了对映体过量 (ee)值,均得到了满意的结果。Tetra-O-acetyl-β-D-glycosyl isothiocyanate was synthesized using α-D-glucose as the starting material through three step reactions and characterized by NMR.Effects of the sort and amount of phase transfer catalysts,reaction time and different solvents on the final yield were discussed.The optimal reaction conditions were:benzene as the solvent,n(2,3,4,6-tetra-O-acetyl-β-D-glycosyl bromide)∶n(KSCN)∶n(benzyltriethylammonium chloride)=1∶2∶1,and reaction time 14 hours.It was used as pre-column chiral derivatizating agent for separating enantiomers and determining the enantiomeric excess of 1,2-diaminocyclohexane with satisfactory result.

关 键 词：吡喃葡萄糖基异硫氰酸酯 硫氰酸钾 相转移催化 

分 类 号：TQ226.25[化学工程—有机化工]