61865-49-4

Basic information

• Product Name: (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester
• Synonyms: (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester;cis-(+/-)-4-(AcetylaMino)-2-Cyclopentene-1-carboxylic Acid Methyl Ester
• CAS NO: 61865-49-4
• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.20442
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 61865-49-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, DMSO, Methanol
• CAS DataBase Reference: (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester(61865-49-4)
• EPA Substance Registry System: (1R,4S)-rel-4-(AcetylaMino)-2-cyclopentene-1-carboxylic Acid Methyl Ester(61865-49-4)

Safety Data

• Hazardous Substances Data: 61865-49-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Carbovir intermediate.

Upstream product

• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 30213-23-1 meso-cyclopent-4-ene-1,3-dicarboxylic acid 
• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 77745-25-6 cis-4-amino-2-cyclopentenecarboxylic acid methyl ester hydrochloride 
• 152279-17-9 (cis)-methyl 4-aminocyclopent-2-enecarboxylate 
• 546-67-8 lead(IV) tetraacetate 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 102579-71-5 cis-4-amino-cyclopent-2-ene-1-carboxylic acid 

Downstream Products

• 65942-42-9 N-((1R,4S)-4-Hydroxymethyl-cyclopent-2-enyl)-acetamide 
• 13190-81-3 N-((1S,3R,4S)-2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-acetamide 
• 13190-81-3 N-((1R,3S,4R)-2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-acetamide 
• 50619-37-9 (-)-(1R,2S,3R,4R)-4-amino-2,3-dihydroxy-1-hydroxymethyl cyclopentane 
• 50619-37-9 (+)-(1S,2R,3S,4S)-4-amino-2,3-dihydroxy-1-hydroxymethyl cyclopentane 
• 141352-48-9 (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol 
• 102579-71-5 (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid 
• 141352-47-8 (1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-carboxylic acid methyl ester 
• 106707-52-2 (1β,2β,3α,5α)-5-Amino-3-hydroxymethyl-1,2-cyclopentanediol 
• 85026-59-1 (-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane 
• 128131-83-9 (+/-)-(trans)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 172721-00-5 (+/-)-trans-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol 

Relevant articles and documents

Substituent and solvent effects in the 1,3-dipolar cycloadditions for synthesis of anti-influenza agent peramivir and its analog

Influenza remains a health problem to humans. Peramivir is a FDA approved anti-influenza drug targeting the virus neuraminidase. The (3 + 2) cycloaddition reaction of 2-ethylbutanenitrile oxide with the cyclopentene dipolarophile derived from Vince lactam is a key step in the conventional synthesis of peramivir. Our study showed that conducting the (3 + 2) cycloaddition reactions with either aliphatic or aromatic nitrile oxide in hexane solution provided high percentage of the desired regioisomer, and the N-substituent having electron-withdrawing property is also beneficial to the regioselectivity. This study also demonstrated an alternative synthetic pathway of (?)-peramivir and the analog having a phenyl group in place of the 3-pentyl moiety.

The Enantioselective Synthesis of an Important Intermediate to the Antiviral, (-)-Carbovir

Two new routes to the important intermediate (-)-8 for the carbocyclic-based nucleosides are reported.The intermediate (-)-8 has also been synthesised in high enantiomeric excess via an enzymatic resolution of the racemic amide (+)-8 or an enzymatic enantiotopic hydrolysis of the meso diester 12.

Synthesis of carbocyclic aminonucleosides

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