Synthesis of 2-Amino-2-deoxy-1,3-dithioidoglycosides via Organocatalytic Relay Glycosylation of 3-O-Acetyl-2-nitrogalactals  

作　　者：Yongyong Wan Lei Deng Liming Wang Yuanhong Tu Hui Liu Jian-song Sun Qingju Zhang 

机构地区：[1]National Research Centre for Carbohydrate Synthesis,Jiangxi Normal University,99 Ziyang Avenue,Nanchang,Jiangxi,330022 China [2]Key Laboratory of Carbohydrate Chemistry and Biotechnology,Ministry of Education,School of Biotechnology,and Wuxi School of Medicine,Jiangnan University,Wuxi,Jiangsu,214122 China

出　　处：《Chinese Journal of Chemistry》2023年第21期2837-2842,共6页中国化学（英文版）

基　　金：This work was financially supported by the National Natural Science Foundation of China(21977039,22007039,22167015);the Science and Technology Department of Jiangxi Province(jxsq2020101084,20212ACB213005);Jiangxi Normal University Innovation Fund(YJS2021010).

摘　　要：Idose-type glycosides have numerous biological activities and have been widely used as anticoagulant drugs and anti-infection drugs.Thioglycosides have enhanced stability for acid-mediated or enzymatic hydrolysis,and have a wide range of applications in glycobiology and drug development.Herein,we describe an efficient method for site-selective and stereoselective synthesis of potential bioactive 2-amino-2-deoxy-1,3-dithioidoglycosides via organocatalysis sequential C3-Ferrier rearrangement and Michael addition of 3-O-acetyl-2-nitrogalactals.Both stepwise and one-pot protocols were carried out and work well.This unique thio-glycosylation protocol highlighted the various advantages,including(i)mild reaction conditions;(ii)excellent site-selectivity and stereoselectivity,good to excellent yields;(iii)broad substrate scopes;(iv)being atom-economic and environmentally friendly;(v)the reactions can be scaled up.

关 键 词：Idoglycosides THIOGLYCOSIDES Stereoselective glycosylation 3-O-Acetyl-2-nitrogalactals ORGANOCATALYSIS Relay glycosylation 

分 类 号：O62[理学—有机化学]