General methods for the synthesis of glycopyranosyluronic acid azides.
Per-O-acetylated D-glycopyranoses derived from both mono- and disaccharides were first converted to glycosyl iodides and subsequently reacted with an azide source to achieve the stereoselective synthesis of beta-D-glycosyl azides after deacetylation. Low-temperature (4 degrees C) TEMPO oxidation of the monosaccharides provided the corresponding uronic acids, which were purified as the free acids. Oxidation of the lactosyl- and cellobiosyl azides resulted in diacid formation. However, 4',6'-O-benzylidene protection enabled selective oxidation of the C-6 hydroxyl. 2-Acetamido-2-deoxy-D-glycopyranosyl azides were also prepared and converted to uronic acids completing the library synthesis.
Ying
Laiqiang
L
Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA.
Gervay-Hague
Jacquelyn
J
D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013696:Temperature; D014574:Uronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*
D001386:Azides; D014574:Uronic Acids