Easy access to 6-membered iminoalditols - important glycosidase inhibitors

Inge Lundt

Research output: Contribution to conferencePosterResearch

Abstract

Stereoselective methods for synthesising iminoalditols are still needed, as this class of compounds is known to contain strong glycosidase inhibitors. We have for some time investigated (1) the possibilities for using 2-amino-6-bromo-2,6-dideoxy-aldonolactones as starting materials for such compounds, since a substitution at C-6 by the 2-amino group should lead to the target molecules. We have found that treatment of mentioned 2-aminolacones with aqueous base gave 5- or 6-membered iminoalditols depending of the stereochemistry of the lactone, while under non aqueous conditions only formation of 6-membered iminoalditols were observed. The use of triethylamine in methanol thus gave methylesters of 6-membered iminouronic acids. Reduction of the ester group with sodium borohydride gave the target compounds. The mechanisms of the reactions will be discussed as well as specific results obtained. (1) Lundt, I. Top. Curr. Chem. 1997, 187, 117-156
Original languageEnglish
Publication date2003
Publication statusPublished - 2003
EventEasy access to 6-membered iminoalditols - important glycosidase inhibitors - 19th Royal Australian Chemical Institute Organic Conference. - Lorna, Australia
Duration: 1 Jan 2003 → …

Conference

ConferenceEasy access to 6-membered iminoalditols - important glycosidase inhibitors
City19th Royal Australian Chemical Institute Organic Conference. - Lorna, Australia
Period01/01/2003 → …

Cite this

Lundt, I. (2003). Easy access to 6-membered iminoalditols - important glycosidase inhibitors. Poster session presented at Easy access to 6-membered iminoalditols - important glycosidase inhibitors, 19th Royal Australian Chemical Institute Organic Conference. - Lorna, Australia, .