405215-53-4

Upstream product

• 501-53-1 benzyl chloroformate 
• 405283-44-5 N-(benzyloxycarbonyl)-1,4-dideoxy-1,4-imino-2,3:5,6-di-O-isopropylidene-D-allitol 
• 117859-46-8 1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-D-allitol 
• 405283-43-4 N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-allitol 

Downstream Products

• 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 
• 674810-55-0 ethyl (E)-N-benzyloxycarbonyl-2,3,4,7-tetradeoxy-4,7-imino-5,6-O-isopropylidene-L-ribo-hept-2-enonate 
• 674810-59-4 ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-altro-heptanonate 
• 674810-60-7 ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate 
• 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 
• 405215-57-8 (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 
• 111193-66-9 (3aR,4R,6aS)-2,2-Dimethyl-4-(toluene-4-sulfonyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 1632124-95-8 (2R,3R,4S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-pyrrolidine-3,4-diol 
• 111265-96-4 (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal 
• 1632125-08-6 C₃₀H₄₆N₄O₄ 

Relevant academic research and scientific papers

Synthesis and cancer growth inhibitory activities of 2-fatty-alkylated pyrrolidine-3,4-diol derivatives

A series of new amphiphilic pyrrolidines containing dodecyl and oleyl apolar side chains were prepared and evaluated for their ability to inhibit the growth of pancreatic ductal adenocarcinoma cells in vitro. The new compounds are shown to exhibit anticancer activity at concentrations in the μM range. ARKAT-USA, Inc.

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).