Asymmetric dihydroxylation of d-glucose derived alpha,beta-unsaturated ester: synthesis of azepane and nojirimycin analogues.
J Org Chem
; 69(14): 4760-6, 2004 Jul 09.
Article
en En
| MEDLINE
| ID: mdl-15230599
ABSTRACT
The asymmetric dihydroxylation of a d-glucose derived alpha,beta-unsaturated ester 3 afforded syn vicinal diols in good to high diastereoselectivity. The conversion of these vicinal diols to the corresponding cyclic sulfate, regio-, stereoselective nucleophilic ring opening by sodium azide, and LAH reduction afforded amino heptitols 7a,b that were converted to azepane 1c,d and nojirimycin analogues 2c,d.
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Banco de datos:
MEDLINE
Asunto principal:
Azepinas
/
Glucosamina
/
Glucosa
Idioma:
En
Año:
2004
Tipo del documento:
Article