173913-65-0

Basic information

• Product Name: (2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester
• Synonyms: (2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester
• CAS NO: 173913-65-0
• Molecular Weight: 489.614
• Mol File: 173913-65-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester(173913-65-0)
• EPA Substance Registry System: (2S,4S)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester(173913-65-0)

Safety Data

• Hazardous Substances Data: 173913-65-0(Hazardous Substances Data)

Upstream product

• 173913-63-8 (2S)-3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester 

Downstream Products

• 174060-99-2 (4S)-4-hydroxy-3,3-dimethyl-pyrrolidine-(2S)-1,2-dicarboxylic acid 1-tert-butyl ester 
• 173913-69-4 (2S)-3,3-dimethyl-N-(9-phenylfluoren-9-yl)proline benzyl ester 
• 174060-98-1 1-(tert-butoxycarbonyl)-3,3-dimethyl-D,L-proline 
• 173913-68-3 (2S,4S)-3,3-Dimethyl-4-methylsulfanylthiocarboxyoxy-1-(9-phenyl-9H-fluoren-9-yl)-pyrrolidine-2-carboxylic acid benzyl ester 

Relevant articles and documents

Regioselective enolization and alkylation of 4-oxo-N-(9-phenylfluoren-9-yl)proline: Synthesis of enantiopure proline-valine and hydroxyproline-valine chimeras

The regioselective enolization of 4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (5) followed by alkylation with different alkyl halides has been used to synthesize a variety of β-alkylproline derivatives. In particular, enolization of 5 with 400 mol % of KN(SiMe3)2 and alkylation with iodomethane provided 3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (7a) in excellent yield. Subsequent hydride reduction of ketone 7a and protecting group exchange by hydrogenation in the presence of di-tert-butyl dicarbonate provided enantiopure (2S,4R)- and (2S,-4S)-3,3-dimethyl-4-hydroxy-N-(BOC)prolines 2. Hydroxyproline-valine chimeras (2S,4R)- and (2S,4S)-2 are each synthesized from hydroxyproline in six steps and 27% respective overall yield. Deoxygenation of 3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl esters 9 via their conversion to xanthates 10 followed by tributylstannane-mediated reduction provided 3,3-dimethyl-N-(9-phenylfluoren-9-yl)proline benzyl ester (11) in excellent yield. Hydrogenation of 11 with Pearlman's catalyst in the presence of di-tert-butyl dicarbonate then furnished (2S)-3,3-dimethyl-N-(BOC)proline (1) in the last step of an eight-step synthesis (41% overall yield) from hydroxyproline. Both proline-valine and hydroxyproline-valine chimeras 1 and 2 were designed to serve as tools for studying the conformational requirements of biologically active peptides.