484686-90-0

Upstream product

• 385766-38-1 ethyl 2-methyl-5-[4-O-(4-methylphenylsulfonyl)-D-arabino-tetritol-1-yl]furan-3-carboxylate 
• 98-59-9 p-toluenesulfonyl chloride 
• 3351-43-7 ethyl 2-methyl-5-(D-arabino-tetritol-1-yl)furan-3-carboxylate 

Downstream Products

• 385766-45-0 (2R,3S,4R)-2-[4-(hydroxymethyl)-5-methylfuran-2-yl]pyrrolidine-3,4-diol 
• 1048667-31-7 ethyl 5-{(1R,2S,3R)-1-azido-2,3-dihydroxy-4-{[(4-methylphenyl)sulfonyl]oxy}butyl}-2-methylfuran-3-carboxylate 
• 385766-39-2 ethyl 5-[(2R,3S,4R)-3,4-dihydroxy-1-(phenylmethyl)pyrrolidin-2-yl]-2-methylfuran-3-carboxylate 
• 484686-94-4 ethyl 5-{(1RS,2S,3R)-1-azido-2,3-dihydroxy-4-{[(4-methylphenyl)sulfonyl]oxy}butyl}-2-methylfuran-3-carboxaldehyde 

Relevant academic research and scientific papers

Synthesis and glycosidase inhibitory activities of 5-(1′,4′-dideoxy-1′,4′-imino-d-erythrosyl)-2- methyl-3-furoic acid (=5-[(3s,4r)-3,4-dihydroxypyrrolidin-2-yl]-2-methylfuran-3-carboxylic acid) derivatives: New leads as selective α-l-fucosidase and β-galactosidase inhibitors

The Garcia-Gonzalez reaction of D-glucose and ethyl acetoacetate generated ethyl 5-[(1′S)-D-erythrosyl]-2-methyl-3-furoate (5), which was converted to ethyl 5-[(1′R)-1′,4′-dideoxy-1′,4′-imino-D- erythrosyl]-2-methyl-3-furoate (3c) and to ethyl 5-[(1′S)-1′,4′-dideoxy-1′,4′-imino-D- erythrosyl]-2-methyl-3-furoate (4c). Similar methods were developed to generate other carboxylic acid derivatives such as methyl (see 3e and 4e), isopropyl (see 3f), and butyl esters (see 3g), S-phenyl (see 3a) and S-ethyl thioesters (see 3m), N-benzylcarboxamides 3b and 4b, glycine-derived amide 3h, and N-phenyl (see 3i), N-isopropyl (see 3j and 4j), N,N-diethyl-(see 3k and 4k), and N-ethyl-carboxamides (see 3l). All the new 5-(1′,4′-dideoxy-1′,4′-imino-D-erythrosyl)-3-furoic acid (=5-[(3S,4R)-3,4-dihydroxypyrrolidin-2-yl)furan-3-carboxylic acid) derivatives 3 and 4 were assayed for inhibitory activity towards 25 commercially available glycosidases. Derivative 3a with a S-phenyl thioester group is a good and selective α-L-fucosidase inhibitor (Ki = 2-4 μM), whereas 4b (with a N-benzylcarboxamide group) is a good β-galactosidase inhibitor.

Synthesis of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic acid derivatives: New leads as selective β-galactosidase inhibitors

The preparation of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives in a stereoselective route starting from D-glucose and ethyl acetoacetate is presented. Ethyl ester (6), N,N-diethylamide (7) and N-isopropylamide (8) have been tested towards 2