Deoxyiminoalditols from Aldonolactones; II. Preparation of 1,4-Dideoxy-1,4-iminohexitols with D- and L-Galacto and D- and L-Ido Configuration: Potential Glycosidase Inhibitors

Inge Lundt; Robert Madsen

doi:10.1055/s-1993-25928

Synthesis 1993; 1993(7): 720-724
DOI: 10.1055/s-1993-25928

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Deoxyiminoalditols from Aldonolactones; II. Preparation of 1,4-Dideoxy-1,4-iminohexitols with D- and L-Galacto and D- and L-Ido Configuration: Potential Glycosidase Inhibitors

Inge Lundt^* , Robert Madsen

^*Department of Organic Chemistry, The Technical University of Denmark, Building 201, DK-2800 Lyngby, Denmark

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

2,6(1,5)-Dibromo-2,6(1,5)-dideoxyhexitols were prepared by reduction of the corresponding 2,6-dibromo-2,6-dideoxyaldono-1,4-lactones with sodium borohydride. Ring closure of the dibromohexitols with aqueous ammonia gave 1,4-dideoxy-1,4-iminohexitols. The reactions were shown to proceed via epoxides. Thus, 1,4-dideoxy-1,4-imino-L-galactitol (3), the corresponding D-isomer 6, and 1,4-dideoxy-1,4-imino-D-iditol (9) and the L-iditol 12 were prepared as the crystalline hydrochlorides.

PDF (456 kb)