187157-74-0

Basic information

• Product Name: (4S,5S)-1-benzyl-5-(2^IV-chloroacetyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester
• Synonyms: (4S,5S)-1-benzyl-5-(2^IV-chloroacetyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester
• CAS NO: 187157-74-0
• Molecular Weight: 551.041
• Mol File: 187157-74-0.mol

Chemical Properties

• CAS DataBase Reference: (4S,5S)-1-benzyl-5-(2^IV-chloroacetyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-1-benzyl-5-(2^IV-chloroacetyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester(187157-74-0)
• EPA Substance Registry System: (4S,5S)-1-benzyl-5-(2^IV-chloroacetyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester(187157-74-0)

Safety Data

• Hazardous Substances Data: 187157-74-0(Hazardous Substances Data)

Upstream product

• 593-71-5 Chloroiodomethane 
• 187157-73-9 (4S,5S)-1-benzyl-2-oxo-3-(9'-phenylfluoren-9'-yl)imidazolidine-4,5-dicarboxylic acid dimethyl ester 
• 191406-43-6 (2S,3S)-2-Benzylamino-3-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester 
• 159434-59-0 dimethyl (2S,3S)-2-azido-3-(9-phenyl-9H-fluoren-9-ylamino)succinate 
• 100-39-0 benzyl bromide 

Downstream Products

• 187157-80-8 (3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione 
• 191406-44-7 (4S,5S)-5-((R)-2-Azido-1-hydroxy-ethyl)-1-benzyl-2-oxo-3-(9-phenyl-9H-fluoren-9-yl)-imidazolidine-4-carboxylic acid 
• 187157-78-4 (4S,5S,1^IVR)-1-benzyl-5-(1^IV-hydroxy-2^IV-azidoethyl)-2-oxo-3-(9''-phenylfluoren-9''-yl)imidazolidine-4-carboxylic acid methyl ester 
• 187157-76-2 (4S,5S)-1-Benzyl-5-((S)-2-chloro-1-hydroxy-ethyl)-2-oxo-3-(9-phenyl-9H-fluoren-9-yl)-imidazolidine-4-carboxylic acid methyl ester 

Relevant articles and documents

Enantiomerically Pure Highly Functionalized α-Amino Ketones from the Reaction of Chiral Cyclic N-(9-Phenylfluoren-9-yl) α-Amido Esters with Organolithium Reagents

The reaction of methyl N-(9-phenylfluoren-9-yl)pyroglutamate with several organolithium reagents afforded the corresponding ketones in excellent yields and with complete retention of enantiomeric purity. The success of this transformation is due to the unusual stability of the tetrahedral intermediates 5, which stems from two factors: the electron-withdrawing effect of the amide nitrogen and the lithium complexing ability of the fluorenyl ring of the 9-phenylfluoren-9-yl group. This ester-to-ketone transformation was also successfully applied to oxazolidinone 9 and imidazolidinone 20 and provided a ketone (21b) that was ultimately transformed into the urea-lactam 26 which incorporates the bicyclic core of streptolidine lactam, a component of the streptrothricin antibiotics.

Enantiospecific synthesis of γ-keto-α,β-diamino acid derivatives. Stereoselective synthesis of a precursor of streptolidine lactam

The reaction of dimethyl (4S,5S)-1-benzyl-2-oxo-3-(9'-phenylfluoren-9'-yl)-imidazolidine 4,5-dicarboxylate (3) with several organolithium reagents afforded the corresponding enantiomerically pure monoketones (4a-e) in good to excellent yields. Chloromethy