Chemical approaches for the stereocontrolled synthesis of 1,2-cis-β-D-rhamnosides / 中国天然药物
Chinese Journal of Natural Medicines (English Ed.)
; (6): 886-901, 2023.
Article
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| WPRIM
| ID: wpr-1011001
Biblioteca responsable:
WPRO
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.
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Texto completo:
1
Índice:
WPRIM
Asunto principal:
Estereoisomerismo
/
Glicosilación
/
Glicósidos
/
Manósidos
Idioma:
En
Revista:
Chinese Journal of Natural Medicines (English Ed.)
Año:
2023
Tipo del documento:
Article