典型文献
2-Diphenylphosphinoyl-acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β-Glycosides
文献摘要：
The configuration of the anomeric glycosidic linkages is crucial for maintaining the biological functions and activities of carbohydrate molecules.However,their stereochemistry control in glycosylation represents one of the most challenging tasks in carbohydrate chemistry.In this report,the easily accessible 2-diphenylphosphinoyl-acetyl(DPPA)group was developed as a highly stereodirecting group for catalytic glycosylation via hydrogen-bond mediated delivery of the alcoholic acceptors.TMSOTf-catalyzed glycosylation with DPPA-installed glycosyl imidate donors displayed excellent β-selectivities and broad substrate scope,particularly practical to synthesize the challenging β-configured 2-deoxy and 2-azido-2-deoxy glycosides from poor acceptors suffering from electron-defi-ciency,steric hindrance,and structural rigidity.Chemoselective removal of the DPPA group could be readily achieved under the mild catalysis of Ni(OTf)2 without affecting acid-or base-labile functional groups,facilitating a rapid conversion to biologically important molecules such as uronic acids and 2,6-deoxy glycosides.The application of this DPPA-directed glycosylation was further highlighted in the complex synthesis toward saponin dioscin using 2,4-O-glycosylated donor in a convergent manner.
文献关键词：
中图分类号：
作者姓名：
Xianglai Liu;Yetong Lin;Ao Liu;Qianhui Sun;Huiyong Sun;Peng Xu;Guolong Li;Yingying Song;Weijia Xie;Haopeng Sun;Biao Yu;Wei Li
作者机构：
Department of Medicinal Chemistry,School of Pharmacy,China Pharmaceutical University,639 Longmian Avenue,Nanjing,Jiangsu 211198,China;State Key Laboratory of Bioorganic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,345 Lingling Road,Shanghai 200032,China
文献出处：
引用格式：
[1]Xianglai Liu;Yetong Lin;Ao Liu;Qianhui Sun;Huiyong Sun;Peng Xu;Guolong Li;Yingying Song;Weijia Xie;Haopeng Sun;Biao Yu;Wei Li-.2-Diphenylphosphinoyl-acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β-Glycosides)[J].中国化学（英文版）,2022(04):443-452
A类：
Diphenylphosphinoyl,Directing,Glycosides,anomeric,stereochemistry,diphenylphosphinoyl,DPPA,stereodirecting,TMSOTf,imidate,azido,Chemoselective,uronic,dioscin
B类：
acetyl,Remote,Group,Highly,Stereoselective,Synthesis,configuration,glycosidic,linkages,crucial,maintaining,functions,activities,carbohydrate,molecules,However,their,control,glycosylation,represents,one,most,challenging,tasks,In,this,report,easily,accessible,was,developed,highly,catalytic,via,hydrogen,bond,mediated,delivery,alcoholic,acceptors,catalyzed,installed,donors,displayed,excellent,selectivities,broad,substrate,scope,particularly,practical,synthesize,configured,deoxy,glycosides,from,poor,suffering,electron,defi,ciency,steric,hindrance,structural,rigidity,removal,could,be,readily,achieved,under,mild,catalysis,without,affecting,base,labile,functional,groups,facilitating,rapid,conversion,biologically,important,such,acids,application,directed,further,highlighted,complex,synthesis,toward,saponin,using,glycosylated,convergent,manner
AB值：
0.564583
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