Selective sulfonylation of 4-C-hydroxymethyl-β-L-threo-pento-1,4- furanose: Synthesis of bicyclic diazasugars

Article abstract of DOI:10.1016/j.tet.2004.03.034

Hydroxymethylation of α-D-xylo-pentodialdose 6 using excess formaldehyde and sodium hydroxide in THF-water (one pot aldol and crossed Cannizzaro reactions) followed by hydrogenolysis of C3-O-benzyl group afforded triol 8. The regio-selective α- and β-sulf