Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide  

作　　者：Lei Cai Jing Zeng Ting Li Ying Xiao Xiang Ma Xiong Xiao Qin Zhang Lingkui Meng Qian Wan 

机构地区：[1]Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation,School of Pharmacy,Huazhong University of Science and Technology,13 Hangkong Road,Wuhan,Hubei 430030,China [2]Institute of Brain Research,Huazhong University of Science and Technology,13 Hangkong Road,Wuhan,Hubei 430030,China

出　　处：《Chinese Journal of Chemistry》2020年第1期43-49,共7页中国化学（英文版）

基　　金：This research is partially supported by the National Natural Science Foundation of China(Nos.21877043,21761132014,21772050,21672077);Wuhan Creative Talent Development Fund,the Fundamental Research Funds for the Central Universities(2019kfyRCPY034,2019JYCXJJ047);Huazhong University of Science and Technology are greatly appreciated.We thank Ana-lytical and Testing Center of HUST for NMR tests.

摘　　要：Summaryof main observation and conclusion A new dehydrativeglycosylation reaction has been established by capitalizing on the compropor-tionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride(Tf2O).By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation,this reagentunderwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group,rendering a transient electrophilic center at the remote site to the anomeric position.The sulfenyltriflate tethered at the ter-minus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion,thereby facilitating the title glycosylation.Aside from accom-modating broad range functional groups and inactive hemiacetal substrates,the present activation protocol also proved expedient for 1,3-diol protection.Most importantly,this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

关 键 词：RENDERING thereby ANHYDRIDE 

分 类 号：O62[理学—有机化学]