405283-44-5

Upstream product

• 117859-46-8 1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-D-allitol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 405215-57-8 (3aR,4S,6aS)-4-{(S)-(tert-Butyl-dimethyl-silanyloxy)-[(1S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-en-3-yl]-methyl}-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 405215-55-6 1,6-anhydro-3,4-dideoxy-3-[(1'S)-N-benzyloxycarbonyl-3',4'-O-isopropylidene-2',5'-dideoxy-2',5'-imino-D-ribitol-1'-C-yl]-D-threo-hex-3-enopyranose 
• 405215-54-5 (3aR,4R,6aS)-4-[(S)-Hydroxy-((1S,5R)-4-oxo-6,8-dioxa-bicyclo[3.2.1]oct-2-en-3-yl)-methyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 674810-60-7 ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate 
• 674810-59-4 ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-altro-heptanonate 
• 674810-55-0 ethyl (E)-N-benzyloxycarbonyl-2,3,4,7-tetradeoxy-4,7-imino-5,6-O-isopropylidene-L-ribo-hept-2-enonate 
• 405215-53-4 N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 
• 405283-43-4 N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-allitol 

Relevant academic research and scientific papers

Stereoselective synthesis of novel tetrahydroxypyrrolizidines

N-Benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 12a has been converted into (1R,2S,6R,7S,7aS)-5 and (1R,2S,6S,7R,7aR)-1,2,6,7- tetrahydroxypyrrolidin-5-ones 6 and (1R,2S,6S,7S,7aS)-7 and (1R,2S,6R,7R,7aS)-1, 2,6,7-tetrahydroxypyrrolizidines 8 following stereoselective paths. These new compounds have been assayed for their inhibitory activities towards 25 glycosidases. Pyrrolizidines 7 and 8 are moderate but selective inhibitors of amyloglucosidase from Rhizopus mold (7: IC50=130μM, K i=120μM; 8: IC50=200μM, Ki=180μM, mixed type of inhibition).

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).