206994-54-9

Basic information

• Product Name: methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate
• Synonyms: methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate
• CAS NO: 206994-54-9
• Molecular Weight: 459.542
• Mol File: 206994-54-9.mol

Chemical Properties

• CAS DataBase Reference: methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate(206994-54-9)
• EPA Substance Registry System: methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate(206994-54-9)

Safety Data

• Hazardous Substances Data: 206994-54-9(Hazardous Substances Data)

Upstream product

• 206994-52-7 methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate 
• 74-88-4 methyl iodide 
• 160882-77-9 (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 1236783-63-3 methyl (2S,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate 
• 1236783-38-2 methyl (2S,3S,4R)-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)-4-(triethylsilyloxy)pyrrolidine-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 

Relevant articles and documents

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.

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).