Synthesis of 3-azido-3-deoxy-beta-d-galactopyranosides.

Summary, in English

Three efficient routes to 3-azido-3-deoxy-beta-d-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-d-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-d-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-d-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-d-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-d-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation.

• Author: Christopher Öberg; Ann-Louise Noresson; Tamara Delaine; Amaia Larumbe; Johan Tejler; Henrik von Wachenfeldt; Ulf Nilsson
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2009
• Language: English
• Pages: 1282-1284
• Publication/Series: Carbohydrate Research
• Volume: 344
• Issue: 11
• Links: http://dx.doi.org/10.1016/j.carres.2009.05.005
• Document type: Journal article
• Publisher: Elsevier
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 1873-426X