Glycerol carbonate in Ferrier reaction: Access to new enantiopure building blocks to develop glycoglycerolipid analogues.
Carbohydr Res
; 436: 1-10, 2016 Dec 21.
Article
em En
| MEDLINE
| ID: mdl-27816891
ABSTRACT
Glycerol carbonate and tri-O-acetyl-D-glucal were used for the synthesis of glycero-functionalized carbohydrates. Ferrier reaction between the two partners afforded the O-glucoside in 84% yield. Spontaneous crystallization yielded 28% of a pure diastereoisomer with the S configuration as determined by X-ray crystallography. Then, the azido-glycerosugar was prepared in two steps:
ring opening of the cyclic carbonate with sodium azide and per-acetylation with an excellent yield of 94%. A library of glycoconjugates were prepared using a 1,3-dipolar cycloaddition in yields ranging from 64 to 99%.Palavras-chave
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Glicoconjugados
/
Carbonatos
/
Glicolipídeos
/
Glicerol
Idioma:
En
Revista:
Carbohydr Res
Ano de publicação:
2016
Tipo de documento:
Article