Selective Axial-to-Equatorial Epimerization of Carbohydrates.
J Am Chem Soc
; 144(26): 11870-11877, 2022 07 06.
Article
en En
| MEDLINE
| ID: mdl-35731921
ABSTRACT
Radical-mediated transformations have emerged as powerful methods for the synthesis of rare and unnatural branched, deoxygenated, and isomeric sugars. Here, we describe a radical-mediated axial-to-equatorial alcohol epimerization method to transform abundant glycans into rare isomers. The method delivers highly predictable and selective reaction outcomes that are complementary to other sugar isomerization methods. The synthetic utility of isomer interconversion is showcased through expedient glycan synthesis, including one-step glycodiversification. Mechanistic studies reveal that both site- and diastereoselectivities are achieved by highly selective H atom abstraction of equatorially disposed α-hydroxy C-H bonds.
Texto completo:
1
Base de datos:
MEDLINE
Asunto principal:
Carbohidratos
/
Azúcares
Tipo de estudio:
Prognostic_studies
Idioma:
En
Revista:
J Am Chem Soc
Año:
2022
Tipo del documento:
Article