Chemical approaches for the stereocontrolled synthesis of 1,2-cis-β-D-rhamnosides.
10.1016/S1875-5364(23)60408-X
- Author:
Juntao CAI
1
;
Xin YUAN
2
;
Yuanfang KONG
3
;
Yulong HU
2
;
Jieming LI
2
;
Shiqing JIANG
4
,
5
;
Chunhong DONG
6
;
Kan DING
7
Author Information
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. Electronic address: juntaocai@hactcm.edu.cn.
2. 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.
3. College of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China.
4. 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; Department of Oncology, The First Affiliated Hospital of Henan University of Chinese Medicine, Zhengzhou 450000, China. Electronic address: jiangshiqing66@
5. com.
6. 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. Electronic address: chunhong_dong@hactcm.edu.cn.
7. 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; 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.
- Publication Type:Review
- Keywords:
1,2-cis-Glycoside;
Carbohydrate;
Glycosylation;
Stereoselectivity;
Total synthesis;
β-Rhamnoside
- MeSH:
Glycosides;
Mannosides;
Glycosylation;
Stereoisomerism
- From:
Chinese Journal of Natural Medicines (English Ed.)
2023;21(12):886-901
- CountryChina
- Language:English
-
Abstract:
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 and Δ-2 effects. Over the past decades, to attain β-stereoselectivity in D-rhamnosylation, researchers have devised numerous direct and indirect methodologies, including the hydrogen-bond-mediated aglycone delivery (HAD) method, the synthesis of β-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 β-D-rhamnosylation and its implications for the total synthesis of tiacumicin B and other physiologically relevant glycans.
