General methods for the synthesis of glycopyranosyluronic acid azides |
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Authors: | Ying Laiqiang Gervay-Hague Jacquelyn |
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Institution: | Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA. |
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Abstract: | 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. |
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Keywords: | Glycosyl azides TEMPO oxidation Uronic acid azides unprotected |
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