Synthese de L'Amino-2-desoxy-2-β-D-arabinopyranoside de Methyle
- 1 January 1984
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 3 (2), 243-251
- https://doi.org/10.1080/07328308408058818
Abstract
No convenient pathway is known to synthesize methyl-2-amino-2-deoxy-D-arabinopyranosides. Methyl-4-O-allyl-2,3-anhydro-β-D-ribopyranoside is easily obtained starting from D-arabinose but the opening of this epoxide with diallylamine is not regioselective, giving both xylo and arabino compounds. We found that participation of the diallylamino group, after mesylation of the mixture, leads to a lyxo aziridinium ion which is regioselectively opened. Trideallylation with palladium on charcoal gives methyl-2-amino-2-deoxy-β-D-arabinopyranosides in good yield.This publication has 18 references indexed in Scilit:
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