1219101-89-9Relevant academic research and scientific papers
Acid-mediated transformations of enantiopure 3,6-dihydro-2H-1,2-oxazines into functionalised aminotetrahydrofuran derivatives
Dekaris, Vjekoslav,Bressel, Bettina,Reissig, Hans-Ulrich
, p. 47 - 50 (2010)
Two new routes to substituted aminotetrahydrofuran derivatives have been investigated. Treatment of 3,6-dihydro-2H-1,2oxazines with hydrochloric acid in the presence of zinc provided 4benzylamino-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-tetrahydro1,2-oxazines were converted into novel tricyclic 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. Georg Thieme Verlag Stuttgart.
