Synthesis of D-hexos-5-uloses by novel in situ hydrolysis of epoxides derived from 6-deoxyhex-5-enopyranosides.
Org Lett
; 2(24): 3929-32, 2000 Nov 30.
Article
em En
| MEDLINE
| ID: mdl-11101456
ABSTRACT
[reaction see text] Epoxides derived from 2,3, 4-tri-O-protected-6-deoxyhex-5-enopyranosides are hydrolyzed in situ to ultimately give novel protected-D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls, 5-ketohexoses) in moderate to high yields. The products adopt a bicyclic structure (1,6-anhydropyranos-5-ulose) in solution with the pyranose ring in (4)C(1) conformation. The methodology has been used to prepare D-xylo-hexos-5-ulose (5-ketoglucose), a synthetic precursor to 1-deoxynojirimycin and a possible intermediate in the biosynthesis of inositols.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Desoxiglucose
/
Compostos de Epóxi
/
Hexoses
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2000
Tipo de documento:
Article
País de afiliação:
Irlanda