Vjekoslav Dekaris, Bettina Bressel, H. Reissig
2010
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0
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1
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Journal
Synlett
Abstract
Two new routes to substituted aminotetrahydrofuran derivatives have been investigated. Treatment of 3,6-dihydro-2H-1,2-oxazines with hydrochloric acid in the presence of zinc provided 4-benzylamino-5-hydroxy furanose derivatives which contain a quaternary anomeric centre with a vinyl unit. Upon mesylation and subsequent heating in aqueous media 5-hydroxy-3,4,5,6-tetrahydro-1,2-oxazines were converted into novel bicyclic 1,2-oxazines with complete regio- and stereoselectivity. Cleavage of the N―O bond and subsequent debenzylation furnished enantiopure polyhydroxylated aminotetrahydrofuran derivatives which are promising ligands for selectin inhibition studies.