Synthesis of an aza analogue of 2-deoxy-D-ribofuranose and its homologues.
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%.
Filichev
V V
VV
Department of Chemistry, University of Southern Denmark, Odense University, DK-5230 Odense M, Denmark.
Brandt
M
M
Pedersen
E B
EB
D000478:Alkylation; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
D001372:Aza Compounds; D003855:Deoxyribose