Chemical approaches for the stereocontrolled synthesis of 1,2-cis-β-D-rhamnosides  

作　　者：CAI Juntao YUAN Xin KONG Yuanfang HU Yulong LI Jieming JIANG Shiqing DONG Chunhong DING Kan 

机构地区：[1]Henan Polysaccharide Research Center,Henan Key Laboratory of Chinese Medicine for Polysaccharides and Drugs Research,Academy of Chinese Medical Sciences,Henan University of Chinese Medicine,Zhengzhou 450046,China [2]College of Pharmacy,Henan University of Chinese Medicine,Zhengzhou 450046,China [3]Department of Oncology,The First Affiliated Hospital of Henan University of Chinese Medicine,Zhengzhou 450000,China [4]Carbohydrate-Based Drug Research Center,CAS Key Laboratory of Receptor Research,State Key Laboratory of Drug Research,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China

出　　处：《Chinese Journal of Natural Medicines》2023年第12期886-901,共16页中国天然药物（英文版）

基　　金：This work was supported by the Natural Science Foundation of Henan Province(No.232300421374),the Science and Technology Research Project of Henan Province(No.222102310231);the Zhongjing Young Scientist Program of Henan University of Chinese Medicine(No.00104311-2022-1-1-70);the Open Project of Key Laboratory of Carbohydrate Chemistry and Biotechnology,Ministry of Education(No.KLCCB-KF202203);the China Postdoctoral Science Fund Project(No.2021M690936).

摘　　要：In carbohydrate chemistry,the stereoselective synthesis of 1,2-cis-glycosides remains a formidable challenge.This complexity is comparable to the synthesis of 1,2-cis-β-D-mannosides,primarily due to the adverse anomeric andΔ-2 effects.Over the past decades,to attainβ-stereoselectivity in D-rhamnosylation,researchers have devised numerous direct and indirect methodologies,including the hydrogen-bond-mediated aglycone delivery(HAD)method,the synthesis ofβ-D-mannoside paired with C6 deoxygenation,and the combined approach of 1,2-trans-glycosylation and C2 epimerization.This review elaborates on the advancements inβ-Drhamnosylation and its implications for the total synthesis of tiacumicin B and other physiologically relevant glycans.

关 键 词：CARBOHYDRATE GLYCOSYLATION 1 2-cis-Glycoside STEREOSELECTIVITY Total synthesis β-Rhamnoside 

分 类 号：R284.2[医药卫生—中药学]