69919-17-1

Basic information

• Product Name: (1R,4S)-methyl 4-acetamidocyclopent-2-enecarboxylate
• CAS NO: 69919-17-1
• Molecular Weight: 183.207
• Mol File: 69919-17-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1R,4S)-methyl 4-acetamidocyclopent-2-enecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S)-methyl 4-acetamidocyclopent-2-enecarboxylate(69919-17-1)
• EPA Substance Registry System: (1R,4S)-methyl 4-acetamidocyclopent-2-enecarboxylate(69919-17-1)

Safety Data

• Hazardous Substances Data: 69919-17-1(Hazardous Substances Data)

Usage

General Description

(1R,4S)-methyl 4-acetamidocyclopent-2-enecarboxylate is a chemical compound with the molecular formula C10H15NO3. It is a derivative of cyclopentene with a methyl and acetamido group attached to the carbon atoms. The compound is a carboxylate ester, meaning that it contains an ester functional group, which is commonly used in the synthesis of pharmaceuticals and agrochemicals. Its stereochemistry is designated as (1R,4S), indicating the configuration of its chiral centers. The compound may have potential applications in various fields, including medicine, agriculture, and material science.

Upstream product

• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 102579-71-5 cis-4-amino-cyclopent-2-ene-1-carboxylic acid 
• 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 
• 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 

Downstream Products

• 65942-42-9 N-((1R,4S)-4-Hydroxymethyl-cyclopent-2-enyl)-acetamide 
• 128131-83-9 (+/-)-(trans)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 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 
• 69979-44-8 (1S,2S,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol 
• 169104-29-4 Acetic acid (1R,4S)-4-acetylamino-cyclopent-2-enylmethyl ester 
• 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.

Biocatalytical Transformations. IV. Enantioselective Enzymatic Hydrolyses of Building Blocks for the Synthesis of Carbocyclic Nucleosides

Enantiomerically pure alkyl (1S,4R)- and (1R,4S)-4-acetamido-cyclopent-2-ene-carboxylates are obtained from their corresponding racemates by hydrolysis with PLE or the lipase from Candida cylindracea.

Synthesis of carbocyclic aminonucleosides

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