糖苷化试剂-糖基三氯乙酰亚胺酯的高效制备

Highly effective preparative method of glycosylation reagents-glycosyl trichloroacetimidates

目的改进糖基三氯乙酰亚胺酯的合成工艺。方法通过碘化钠催化的Finkelstein反应代替银盐,降低了成本,以体积分数3%三乙胺处理的中性氧化铝代替硅胶柱色谱处理粗产物避免了糖基三氯乙酰亚胺酯的分解,使反应总收率达到70%以上。结果分别以D-葡萄糖、L-鼠李糖、L-阿拉伯糖、D-木糖、D-甘露糖、D-半乳糖、D-阿拉伯糖为原料,共合成了7个糖基三氯乙酰亚胺酯,它们的结构经1H-NMR、13C-NMR和MS确证。结论该制备工艺适合多种糖基三氯乙酰亚胺酯的大量制备,与文献报道的工艺相比,改进后的工艺更为经济、安全、简便、收率高。

Objective To improve preparation procedure of glycosyl trichloroacetimidates. Methods Finkel- stein reaction catalysted by NaI and handling the crude product with neutral aluminium oxide can increase the yields. The total yields were over 70%. Results By using D-glocose, L-rhamanose, L-arabinose, D-xy- lose, D-mannose, D-galactose and D-arabinose as starting materials, seven glycosyl trichloroacetimidates were synthesized. Their structures were confirmed by ^1H-NMR, lsC-NMR and MS. Conclusions This preparation method is suitable for large-scale preparation of various glycosyl trichloroacetimidates. Compared to reported method, this improved preparation procedure is more economic, safer and of higher yield.