Stereoselective syntheses of the O,N-protected subunits of the tunicamycins.
Carbohydr Res
; 299(4): 245-52, 1997 Apr 30.
Article
em En
| MEDLINE
| ID: mdl-9175272
ABSTRACT
The synthesis of the title compounds is described, i.e. coupling of the ylide, generated from the iodophosphonium salt of protected N-phthaloyl-D-galactosamine with 2,3-O-isopropylidene D-ribo-aldehyde afforded an undecose in high yield. Hydroboration-oxidation reaction of the olefinic linkage in the undecose led to the desired tunicamine, as the predominant product. After conversion of the latter to a glycosyl acceptor, this was assembled with the fully protected 2-oxyimino-2-deoxy-alpha-D-arabino-hexopyranosyl bromide, leading to a trehalose-type alpha, beta-disaccharide.
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Base de dados:
MEDLINE
Assunto principal:
Tunicamicina
/
Dissacarídeos
/
Galactosamina
Idioma:
En
Ano de publicação:
1997
Tipo de documento:
Article