一个正交保护的岩藻糖乙硫苷供体的合成

Synthesis of ethyl 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside

目的 合成3-氧-叔丁基二甲基硅基-4-氧-苯甲酰基-2-氧-对甲氧基苄基-α-L-岩藻糖乙硫苷供体。方法 以L-岩藻糖硫苷为原料,通过异亚丙基化、对甲氧基苄基化、苯甲酰基化等6步反应得到了正交保护的目标化合物;利用~1HNMR、CNMR和LC-MS(ESI)验证目标化合物的结构。结果与结论 最终以35%的总收率得到了目标化合物,为含有岩藻糖的天然产物的合成提供了很好的中间体。

OBJECTIVE To synthesize 4-O-benzoyl-3-O-tert-butyldimethylsilyl-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside.METHODS 1-thio-β-L-fucopyranoside was used as raw material, and the orthogonal protected target compound was obtained through six steps of isopropylation, p-methoxy benzylation and benzoylation.The structure of this target compound was confirmed by ~1HNMR,CNMR and LC-MS(ESI).RESULTS and CONCLUSION Finally, the target compound has been obtained with a total yield of 35%.The protected target is a good intermediate for the synthesis of natural products containing fucose.