Preparation of N-nosyl-3,4-epimines derived from levoglucosan by sodium borohydride reduction.
Starting from 1,6-anhydro-beta-d-glucopyranose 1 (levoglucosan), N-o-nitrobenzenesulfonyl (nosyl) 3,4-epimino derivatives with d-allo, d-galacto, and d-talo configurations have been prepared via NaBH(4) reduction of suitably substituted azido tosylates. The benefits and limitations of this method over the classical LiAlH(4) reduction method are discussed.
Kroutil
Jirí
J
Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, CZE-128 43 Prague 2, Czech Republic. kroutil@natur.cuni.cz
Karban
Jindrich
J
D001894:Borohydrides / Q000737:chemistry*; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D009578:Nitrobenzenes / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
D001894:Borohydrides; D009578:Nitrobenzenes; C014989:1,6-anhydro-beta-glucopyranose; C025364:sodium borohydride; D005947:Glucose