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

文献类型：期刊论文

作者Cai, Juntao4; Yuan, Xin4; Kong, Yuanfang3; Hu, Yulong4; Li, Jieming4; Jiang, Shiqing2,4; Dong, Chunhong4; Ding, Kan1,4
刊名CHINESE JOURNAL OF NATURAL MEDICINES
出版日期2023-12-01
卷号21期号:12页码:886-901
关键词Carbohydrate Glycosylation 1,2-cis-Glycoside Stereoselectivity Total synthesis /I-Rhamnoside
ISSN号2095-6975
DOI10.1016/S1875-5364(23)60408-X
通讯作者Cai, Juntao(juntaocai@hactcm.edu.cn) ; Jiang, Shiqing(jiangshiqing66@126.com) ; Dong, Chunhong(chunhong_dong@hactcm.edu.cn)
英文摘要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-/I-D-mannosides, primarily due to the adverse anomeric and Delta-2 effects. Over the past decades, to attain /I-stereoselectivity in D-rhamnosylation, researchers have devised numerous direct and indirect methodologies, including the hydrogen-bond-mediated aglycone delivery (HAD) method, the synthesis of /I-D-mannoside paired with C6 deoxygenation, and the combined approach of 1,2-trans-glycosylation and C2 epimerization. This review elaborates on the advancements in /I-D-rhamnosylation and its implications for the total synthesis of tiacumicin B and other physiologically relevant glycans.
WOS关键词REDUCTIVE RADICAL FRAGMENTATION ; TRISACCHARIDE REPEATING UNIT ; O-SPECIFIC POLYSACCHARIDE ; BETA-D-RHAMNOPYRANOSIDES ; STEREOSELECTIVE-SYNTHESIS ; VERSATILE APPROACH ; GLYCOSYL DONORS ; D-RHAMNOSIDES ; LIPOPOLYSACCHARIDE ; XANTHOMONAS
资助项目Natural Science Foundation of Henan Province[232300421374] ; Science and Technology Research Project of Henan Province[222102310231] ; Zhongjing Young Scientist Program of Henan University of Chinese Medicine[00104311-2022-1-1-70] ; Open Project of Key Laboratory of Carbohydrate Chemistry and Bio-technology, Ministry of Education[KLCCB-KF202203] ; China Postdoctoral Science Fund Project[2021M690936]
WOS研究方向Integrative & Complementary Medicine ; Pharmacology & Pharmacy
语种英语
WOS记录号WOS:001146010900001
出版者CHINESE JOURNAL NATURAL MEDICINES
源URL[http://119.78.100.183/handle/2S10ELR8/308799]  
专题中国科学院上海药物研究所
通讯作者Cai, Juntao; Jiang, Shiqing; Dong, Chunhong
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, Carbohydrate Based Drug Res Ctr, CAS Key Lab Receptor Res,State Key Lab Drug Res, Shanghai 201203, Peoples R China
2.Henan Univ Chinese Med, Affiliated Hosp 1, Zhengzhou 450000, Henan, Peoples R China
3.Henan Univ Chinese Med, Coll Pharm, Zhengzhou 450046, Peoples R China
4.Henan Univ Chinese Med, Henan Key Lab Chinese Med Polysaccharides & Drugs, Henan Polysaccharide Res Ctr, Acad Chinese Med Sci, Zhengzhou 450046, Peoples R China
推荐引用方式
GB/T 7714		 Cai, Juntao,Yuan, Xin,Kong, Yuanfang,et al. Chemical approaches for the stereocontrolled synthesis of 1,2-cis-β-D-rhamnosides[J]. CHINESE JOURNAL OF NATURAL MEDICINES,2023,21(12):886-901.
APA Cai, Juntao.,Yuan, Xin.,Kong, Yuanfang.,Hu, Yulong.,Li, Jieming.,...&Ding, Kan.(2023).Chemical approaches for the stereocontrolled synthesis of 1,2-cis-β-D-rhamnosides.CHINESE JOURNAL OF NATURAL MEDICINES,21(12),886-901.
MLA Cai, Juntao,et al."Chemical approaches for the stereocontrolled synthesis of 1,2-cis-β-D-rhamnosides".CHINESE JOURNAL OF NATURAL MEDICINES 21.12(2023):886-901.

入库方式： OAI收割

来源：上海药物研究所

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