Chemical approaches for the stereocontrolled synthesis of 1,2-cis-ß-D-rhamnosides.
Chin J Nat Med
; 21(12): 886-901, 2023 Dec.
Article
in En
| MEDLINE
| ID: mdl-38143103
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-ß-D-mannosides, primarily due to the adverse anomeric and Δ-2 effects. Over the past decades, to attain ß-stereoselectivity in D-rhamnosylation, researchers have devised numerous direct and indirect methodologies, including the hydrogen-bond-mediated aglycone delivery (HAD) method, the synthesis of ß-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 ß-D-rhamnosylation and its implications for the total synthesis of tiacumicin B and other physiologically relevant glycans.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Glycosides
/
Mannosides
Language:
En
Journal:
Chin J Nat Med
Year:
2023
Document type:
Article