Self-assembled hexameric capsule:A highlyβ-selective O-glycosylation reaction enabled via proton wire mechanism  

作　　者：Kuppusamy Kanagaraj Julius Rebek Jr. Yang Yu 

机构地区：[1]Center for Supramolecular Chemistry&Catalysis and Department of Chemistry,College of Science,Shanghai University,Shanghai,200444,China [2]The Skaggs Institute for Chemical Biology and Department of Chemistry,The Scripps Research Institute,La Jolla,CA 92037,United States

出　　处：《Green Synthesis and Catalysis》2023年第1期7-9,共3页绿色合成与催化（英文）

基　　金：This work was supported by the National Natural Science Foundation of China(Nos.22071144 and 21801164);by Shanghai Scientific and Technological Committee(No.22010500300).

摘　　要：A simple methodology has been developed for the synthesis of highlyβ-selective O-glycosylation scaffolds of wider substrate scope under mild conditions using a self-assembled hexameric capsule.The reaction conditions are compatible with a wide range of functional groups.Extensive control experiments and theoretical studies established that the reaction takes place inside the capsule cavity.The substrates are activated via a proton wire as seen in some enzymes,and the reactions follow an SN2 pathway through a loose transition state.The advantages of this methodology are selectivity,high yields and scalability;the catalyst is readily recovered and reused.The methodology was adapted to the synthesis of mesomorphic glycosides and anti-tumour agents in short synthetic routes.

关 键 词：CAPSULE Self-assembly β-Selective glycosylation Synthetic receptor Proton wire mechanism 

分 类 号：O62[理学—有机化学]