Wiley-VCH Verlag, ChemInform, 39(34), 2003
Elsevier, Tetrahedron, 24(59), p. 4261-4273
DOI: 10.1016/s0040-4020(03)00631-8
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N-Benzyl-N-glycosylhydroxylamines were prepared in very good yield via condensation of furanoses and pyranoses with N-benzylhydroxylamine at 110°C for 30 min under solvent-free conditions. These anomeric sugar-hydroxylamines exist in equilibrium with the open-chain nitrone form. In fact upon treatment with various organometallic reagents, the corresponding adducts were obtained with good to high diastereoselectivity. These adducts were converted into iminosugar-C-glycosides by reductive dehydroxylation and intramolecular cyclization.