147698-13-3

Upstream product

• 493039-08-0 methyl (4S)-4-[N-(9-phenyl-9-fluorenyl)amino]-1-cyclopentenecarboxylate 
• 147780-42-5 (1S,3S)-1--3-(methoxycarbonyl)cyclopentane 
• 147698-08-6 (S)-6-Imidazol-1-yl-6-oxo-5-(9-phenyl-9H-fluoren-9-ylamino)-hexanoic acid methyl ester 
• 147698-06-4 1-tert-Butyl 6-methyl (S)-2-[N-(9-phenylfluoren-9-yl)amino]hexandioate 
• 215182-84-6 (1S,3R/S)-1-[N-(9-Phenylfluoren-9-yl)amino]-2-oxo-3-(methoxycarbonyl)cyclopentane 
• 147698-07-5 (S)-2-hexanedioic acid γ-methyl ester 
• 147698-10-0 (S)-3--(methoxycarbonyl)cyclopentene 
• 55135-66-5 9-bromo-9-phenyl-9H-fluorene 
• 493039-10-4 (1S)-1-[N-(9-phenyl-9-fluorenyl)amino]-3-(hydroxymethyl)-cyclopentene 
• 147698-11-1 (1S,3R)-1--3-(methoxycarbonyl)cyclopentane 
• 147698-12-2 (S)-3--1-(hydroxymethyl)cyclopentene 

Downstream Products

• 117957-62-7 (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanone 

Relevant academic research and scientific papers

An efficient procedure for the preparation of (1S,3R)- and (1S,3S)-1-amino-3-(hydroxymethyl)cyclopentanes

Enantiomerically pure (1S,3S)- and (1S,3R)-1-amino-3-(hydroxymethyl) cyclopentanes have been efficiently synthesized from L-aspartic acid. The title compounds are isosteres of ribose and may be used to construct nucleoside analogs with important antiviral

Chirospecific Synthesis of (1S,3R)-1-Amino-3-(hydroxymethyl)cyclopentane, Precursor for Carbocyclic Nucleoside Synthesis. Dieckmann Cyclization with an α-Amino Acid

Carbocyclic nucleosides are important isosters of nucleosides possessing a variety of antiviral and antineoplastic activities.We report here a new method for the chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.This compound is a key precursor for the synthesis of some carbocyclic nucleosides.The method involves (1) an improved synthesis of (S)-2-aminoadipic acid; (2) Dieckmann cyclization of this α-amino acid to an aminocyclopentanone; and (3) elaboration of the latter to the target (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.The starting (S)-2-aminoadipic acid δ-methyl ester was prepared enantiomerically pure from (S)-aspartic acid in 51percent overall yield.Dieckmann condensation converted this amino acid to a (methoxycarbonyl)-cyclopentanone, and reduction of the ketone followed by elimination yielded (S)-3--1-(methoxycarbonyl)cyclopentene.Reduction of the double bond gave a mixture of the cis and trans diastereomers.This mixture was converted to a single diastereomer by epimerization and trapping of the cis isomer as (1S,4R)-2-(9-phenylfluoren-9-yl)-2-azabicycloheptan-3-one.Hydrolytic cleavage of the lactam followed by reduction gave (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.