147698-07-5

Basic information

• Product Name: (S)-2-hexanedioic acid γ-methyl ester
• Synonyms: (S)-2-hexanedioic acid γ-methyl ester
• CAS NO: 147698-07-5
• Molecular Weight: 415.489
• Mol File: 147698-07-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-hexanedioic acid γ-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-hexanedioic acid γ-methyl ester(147698-07-5)
• EPA Substance Registry System: (S)-2-hexanedioic acid γ-methyl ester(147698-07-5)

Safety Data

• Hazardous Substances Data: 147698-07-5(Hazardous Substances Data)

Upstream product

• 147698-04-2 1-tert-Butyl 6-methyl (S)-2-hex-4-enedioate 
• 55135-66-5 9-bromo-9-phenyl-9H-fluorene 
• 147698-06-4 1-tert-Butyl 6-methyl (S)-2-[N-(9-phenylfluoren-9-yl)amino]hexandioate 

Downstream Products

• 147698-12-2 (S)-3--1-(hydroxymethyl)cyclopentene 
• 147698-10-0 (S)-3--(methoxycarbonyl)cyclopentene 
• 215182-84-6 (1S,3R/S)-1-[N-(9-Phenylfluoren-9-yl)amino]-2-oxo-3-(methoxycarbonyl)cyclopentane 
• 1400583-12-1 (1S,4R)-4-tert-Butoxycarbamoyl-1-methoxycarbonylcyclopentane 
• 329910-39-6 (1S,3S)-1-(tert-butoxycarbonylamino)cyclopentane-3-carboxylic acid methyl ester 
• 147698-13-3 (1S,3R)-1--3-(hydroxymethyl)cyclopentane 
• 147780-43-6 (1S,3S)-1--3-(hydroxymethyl)cyclopentane 
• 147698-11-1 (1S,3R)-1--3-(methoxycarbonyl)cyclopentane 
• 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 

Relevant articles and documents

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.