405215-61-4

Upstream product

• 117770-10-2 2,3-bis-(O-tert-butyldimethylsilyl)-1,4-dideoxy-5,6-O-isopropylidene-1,4-imino-D-glucitol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 405215-63-6 (-)-N-benzyloxycarbonyl-2,3-di-O-[tert-butyldimethylsilyl]-1,4-dideoxy-1,4-imino-D-glucitol 

Relevant academic research and scientific papers

Synthesis of (1→3)-C and homo(1→3)-C-linked imino-disaccharides starting from levoglucosenone and isolevoglucosenone

The reaction of 2,5-(benzyloxycarbonyl)imino-2,5-dideoxy-3,4-O-isopropylidene-L-ribose ((-)-15) with levoglucosenone (5) in the presence of Et2A1I 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-hexo-pyranoside ((+)-22). The addition of benzyl alcohol to isolevoglucosenone (3), followed by cross-aldol condensation with 3,6-[tert-butoxycarbonyl]imino-2,3,6trideoxy-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).