179990-60-4

Basic information

• Product Name: (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester
• Synonyms: (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester
• CAS NO: 179990-60-4
• Molecular Weight: 401.462
• Mol File: 179990-60-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester(179990-60-4)
• EPA Substance Registry System: (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester(179990-60-4)

Safety Data

• Hazardous Substances Data: 179990-60-4(Hazardous Substances Data)

Upstream product

• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 160882-77-9 (2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 179990-59-1 (2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 160882-76-8 (2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 55135-66-5 9-bromo-9-phenyl-9H-fluorene 

Downstream Products

• 114976-76-0 1,4-dideoxy-1,4-imino-D-mannitol hydrochloride 
• 179990-51-3 1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone 
• 179990-54-6 1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-fluoro-ethanone 
• 179990-52-4 1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-methoxymethoxy-ethanone 
• 179990-53-5 1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-3-[1,3]dioxolan-2-yl-propan-1-one 
• 180182-43-8 (S)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanol 
• 179990-58-0 (R)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanol 
• 180182-37-0 (S)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-fluoro-ethanol 
• 179990-57-9 (R)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-fluoro-ethanol 
• 180182-35-8 (S)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-methoxymethoxy-ethanol 
• 179990-55-7 (R)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-methoxymethoxy-ethanol 
• 179990-56-8 (S)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-3-[1,3]dioxolan-2-yl-propan-1-ol 
• 179990-61-5 (3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid methyl ester 

Relevant articles and documents

Enantiospecific and stereoselective synthesis of polyhydroxylated pyrrolidines and indolizidines from trans-4-hydroxy-L-proline

We have developed a short, efficient, and stereoselective synthesis of polyhydroxylated pyrrolidine and indolizidine glycosidase inhibitors starting from 4-hydroxy-L-proline. The regio- and stereoselective hydroxylation of an N-Pf-4-oxoproline enolate and the stereoselective reduction of the resulting keto alcohol allowed us to introduce the cis diol present in the target compounds. The different side chains needed to complete the syntheses of the target compounds were introduced by reduction of the ester group of a substituted proline or by reaction of organolithium or organomagnesium reagents with the same group followed by stereoselective reduction of the resulting ketones. Hydrogenolysis of the alcohols thus obtained gave the hydrochlorides of the desired pyrrolidine glycosidase inhibitors, which were obtained in nine steps in overall yields greater than 50%. The indolizidine glycosidase inhibitor 8-epi-swainsonine was also prepared using this approach.