Stereocontrolled synthesis of α-d-allulofuranosides using α-selective d-fructofuranosidation reaction.
Carbohydr Res
; 536: 109044, 2024 Feb.
Article
en En
| MEDLINE
| ID: mdl-38325068
ABSTRACT
Stereocontrolled synthesis of rare sugar derivatives, namely α-d-allulofuranosides, was achieved using d-fructose, one of the most abundant carbohydrates in nature. The following are the key steps of the α-d-allulofuranosides' synthesis. (1) An α-selective glycosidation reaction of 1,3,4,6-tetra-O-benzoylated d-fructofuranosyl donor to obtain α-d-fructofuranosides with 98 %-75 % isolated yields. (2) A regioselective 1,4,6-tri-O-pivaloylation reaction of the tetraol of α-d-fructofuranosides with the C3-hydroxy group remaining intact. (3) The oxidation of the C3-hydroxy group followed by the stereoselective reduction of the C3-carbonyl group. Primary and secondary alcohols and sugars can be used as glycosyl acceptors and aglycones for the following pivaloylation and stereoinversion reactions to obtain α-d-allulofuranosides.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Carbohidratos
/
Alcoholes
Idioma:
En
Revista:
Carbohydr Res
Año:
2024
Tipo del documento:
Article
País de afiliación:
Japón
Pais de publicación:
Países Bajos