Synthesis of an aza analogue of 2-deoxy-d-ribofuranose and its homologues Original Research Article

Azasugars were obtained in one-pot reactions by catalytic reduction reactions of amino group precursors in aldosugars followed by intramolecular reductive amino alkylation reactions. (3R,4S)-4-[(1S)-1,2-Dihydroxyethyl]pyrrolidin-3-ol was obtained from d-xylose by two different strategies through 3-C-cyano-3-deoxy-d-ribo-pentofuranose or 3-C-azidomethyl-3-deoxy-d-ribo-pentofuranose in 6 and 16% overall yields, respectively. The oxidative cleavage of the diol group in the corresponding Fmoc-azasugar followed by deprotection afforded (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4S)-4-[(1S,2R)-1,2,3-Trihydroxypropyl]pyrrolidin-3-ol was synthesized from diacetone-d-glucose through 3-deoxy-3-C-nitromethyl-d-allose and the overall yield was 7%.