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■ Synthesis of (1→3)-C and Homo-(1→3)-C-linked Imino-disaccharides Starting from Levoglucosenone and Isolevoglucosenone

Christian Marquis, Francesca Cardona, Inmaculada Robina, Gaby Wurth, and Pierre Vogel*

*Section de Chimie de l‘Universié de Lausanne, BCH, CH-1015 Lausanne-Dorigny, Switzerland

Abstract

The reaction of 2,5-(benzyloxycarbonyl)imino-2,5-dideoxy-3,4-O-isopropylidene-L-ribose ((-)-15) with levoglucosenone (5) in the presence of Et₂AlI gave a 3,4-dideoxy-D-glycero-hex-3-enopyranos-2-ulose derivative ((-)-16) that was converted into the (1→3)-C-linked imino-disaccharide: methyl 3,4-dideoxy-3-[(1’S)-2’,5’-dideoxy-2’,5’-imino-D-ribitol-1’-C-yl)-α-D-lyxo-hexopyranoside ((+)-22). The addition of benzyl alcohol to isolevoglucosenone (3), followed by cross-aldol condensation with 3,6-[tert-butoxycarbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose ((+)-30) generated, after water elimination, a single enone ((+)-31) that was converted into a homo-(1→3)-C-linked imino-disaccharide: 3-deoxy-3-(1’,2’,3’,6’-tetradeoxy-3’,6’-imino-L-arabino-hexitol-1’-C-yl)-β-D-galactofuranose (44).