Chain extension of sugar delta-lactones with the enolate of tert-butyl bromoacetate and elaboration into functionalized C-ketosides, C-glycosides, and C-glucosyl glycines.
Org Lett
; 3(25): 4115-8, 2001 Dec 13.
Article
em En
| MEDLINE
| ID: mdl-11735598
ABSTRACT
[structure see text] We describe the synthesis of a series of exocyclic sugar epoxides 1 prepared in a one-step procedure from sugar delta-lactones with the enolate of tert-butyl bromoacetate. Ring opening of the sugar oxiranes provides C-ketosides while reduction affords functionalized C-glycosides bearing an alpha-hydroxy ester moiety. The alpha-hydroxy ester can be converted into C-glucosyl glycine analogues 2.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos de Epóxi
/
Glicosídeos
/
Lactonas
/
Acetatos
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2001
Tipo de documento:
Article
País de afiliação:
Japão