206994-52-7

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 160882-77-9 (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 206994-54-9 methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate 
• 206994-55-0 (2S,3R)-3-Methoxymethoxy-4-methylene-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid methyl ester 
• 1236783-56-4 methyl (2S,3S)-3-(methoxymethoxy)-3-methyl-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate 
• 1236783-60-0 methyl (S)-4-methoxy-3-(methoxymethoxy)-1-(9-phenyl-9H-fluoren-9-yl)-2,5-dihydro-1H-pyrrole-2-carboxylate 
• 206994-58-3 (2S,3S,4R)-4-Acetoxy-3-methoxymethoxy-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid methyl ester 
• 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).

Total synthesis of depsilairdin

(Figure presented) The total synthesis of depsilairdin, a host-selective phytotoxin isolated from Leptosphaeria maculans (the causal agent of blackleg disease of oilseed Brassicas), has been achieved by N-terminal extension of a suitably protected derivative of the hitherto unknown amino acid (2S,3S,4R)-3,4-dihydroxy-3-methyl-proline (Dhmp) followed by esterification with lairdinol A. The latter esterification, complicated by the sterically hindered nature of the carboxyl group, was accomplished by a novel method involving reaction of the 1-hydroxybenzotriazole (HOBt) derived active ester with the bromomagnesium alkoxide of lairdinol A. Three depsilairdin analogues were also prepared by replacing the Dhmp residue with l-proline and cis- and trans-4-hydroxy-l-proline. Phytotoxicity assays showed that the analogues were nontoxic to both blackleg-susceptible (brown mustard) and -resistant (canola) plants, suggesting that the presence of the Dhmp residue in depsilairdin is important for its host-selective toxicity toward brown mustard.