206994-57-2

Upstream product

• 160882-77-9 (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 206994-55-0 (2S,3R)-3-Methoxymethoxy-4-methylene-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 206994-59-4 [(2R,3R,4S)-4-Hydroxymethyl-3-methoxymethoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidin-2-yl]-methanol 

Relevant academic research and scientific papers

C-3- and C-4-alkylated polyhydroxypyrrolidines: Enantiospecific syntheses and glycosidase inhibitory activity

Short, efficient, and stereoselective syntheses of enantiomerically pure C-3- and C-4-alkylated analogues of (2R,3S,4R)-3,4-dihydroxy-2- (hydroxymethyl)pyrrolidine, a potent α-galactosidase inhibitor, from 4- hydroxy-L-proline are presented. Grignard addition or enolate alkylation of a N-(9-phenylfluoren-9-yl)-4-oxo-3-[(methoxymethyl)oxy]proline and epoxidation or hydroboration of a 4-methylene-3-[(methoxymethyl)oxy]proline proceeded with complete stereoselection and in excellent yields. The inhibitory activities of the synthesized pyrrolidines were measured and showed that the fit of A. niger α-galactosidase and the jack bean α-mannosidase around C-3 of the pyrrolidine ring (α face) must be very tight, while the fit around C- 4 (α face) is much looser. Positioning a methylene group between the hydroxyl at C-4 and the pyrrolidine ring completely abolishes the inhibitory activity (see analogue 5).