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 β-D-glycosyl azides after deacetylation. Low-temperature (4°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.
Original language | English (US) |
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Pages (from-to) | 835-841 |
Number of pages | 7 |
Journal | Carbohydrate Research |
Volume | 338 |
Issue number | 9 |
DOIs | |
State | Published - Apr 22 2003 |
Keywords
- Glycosyl azides
- TEMPO oxidation
- Uronic acid azides, unprotected
ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry