Asymmetric synthesis of amino sugars. Part 2.† A novel versatile approach to the chiral non-racemic synthesis of 2-amino-2-deoxy sugars. Preparation of L-glucosamine, L-mannosamine and L-talosamine derivatives
- 5 May 2000
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 15,p. 2465-2473
- https://doi.org/10.1039/b001721n
Abstract
A novel methodology for asymmetric synthesis of 2-amino-2-deoxy sugars is developed, starting from readily available chiral building block 1 and 2,3-O-isopropylideneglyceraldehyde 2, via Julia olefination and subsequent dihydroxylation as key steps. The versatility of this approach is exemplified by the preparation of L-glucosamine, L-mannosamine and L-talosamine derivatives in highly diastereometrically pure forms.Keywords
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