L-葡萄糖氟苷的合成

Synthesis of L-glucosyl fluoride

目的 对L-葡萄糖氟苷进行合成研究,以通过化学手段解决稀有L-葡萄糖类化合物的来源问题。方法利用“首尾翻转”策略,经异头位的相转移催化反应、羟甲基氧化、脱羧氟代等关键反应步骤,完成目标化合物的合成。结果 以商业可得的2,3,4,6-四-O-苄基-D-吡喃葡萄糖半缩醛为原料,通过在异头位引入丙二腈基团发展了1种合成L-葡萄糖氟苷的新方法。经9步以9%的总收率合成了L-葡萄糖氟苷,为L-葡萄糖氟苷糖基供体的合成提供了方法学基础。

Objective The synthesis research on L-glucosyl fluoride was finished,which gave a convenient approach to synthesize the derivatives of L-glucose by chemical method.Methods According to “head-to-tail inversion” strategy,the target molecues were achieved by using phase transfer catalytic reaction,oxidation of hydroxymethyl and decarboxylation fluoride substitution.Results A new method for the synthesis of L-glucosyl fluoride was developed by introducing a malononitrile at anomeric position of 2,3,4,6-tetra-O-benzyl-Dglucopyranose in 9% yield over total 9 steps,which laid a solid foundation for the synthesis of corresponding glycosyl donors.