136470-79-6

Basic information

• Product Name: 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1R-cis)-
• Synonyms: 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1R,4S)-;2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1R-cis)-;(1R,4S)-4-[2-AMino-6-(cyclopropylaMino)-9H-purin-9-yl]-2-cyclopentene-1-Methanol;(1R,4S)-Abacavir;(1R-cis)-4-[2-AMino-6-(cyclopropylaMino)-9H-purin-9-yl]-2-cyclopentene-1-Methanol;ent-Abacavir
• CAS NO: 136470-79-6
• Molecular Formula: C14H18N6O
• Molecular Weight: 286.33
• Product Categories: Anti-virals;Bases & Related Reagents;Inhibitors;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Anti-virals, Inhibitors, Nucleotides, Bases & Related Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 136470-79-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 636.0±65.0 °C(Predicted)
• Appearance: /
• Density: 1.70±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 14.86±0.10(Predicted)
• CAS DataBase Reference: 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1R-cis)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1R-cis)-(136470-79-6)
• EPA Substance Registry System: 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1R-cis)-(136470-79-6)

Safety Data

• Hazardous Substances Data: 136470-79-6(Hazardous Substances Data)

Usage

Uses

The enatiomer of the nucleoside reverse transcriptase inhibitor (NRTI) Abacavir (A105000) with similar antiviral properties.

Upstream product

• 178456-36-5 ((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate 
• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 765-30-0 Cyclopropylamine 
• 171887-04-0 (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene 
• 172015-79-1 ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride 
• 10310-21-1 2-Amino-6-chloropurin 
• 268737-86-6 cis-3-benzoyloxy-4-(hydroxymethyl)cyclopentene 
• 136470-88-7 (-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide 
• 143395-28-2 (1R,5R)-5-hydroxymethyl-2-cyclopenten-1-ol 
• 120503-69-7 2-amino-6-(cyclopropylamino)purine 
• 162992-44-1 9-[cis-(1'R,4'S)-4'-acetoxymethyl-2'-cyclopenten-1'-yl]-9H-2-amino-6-chloropurine 
• 178456-34-3 (1R,2R)-2-acetoxy-1-(acetoxymethyl)-3-cyclopentene 
• 178327-18-9 [3(1R,2R),4S]-4-benzyl-3-(2-hydroxycyclopent-3-enecarbonyl)oxazolidin-2-one 
• 178327-17-8 [3(2S,4R),4S]-3-(2-allyl-3-hydroxypent-4-enoyl)-4-benzyloxazolidin-2-one 

Relevant articles and documents

Synthesis and Antiviral Evaluation of TriPPPro-AbacavirTP, TriPPPro-CarbovirTP, and Their 1′,2′-cis-Disubstituted Analogues

Herein we describe the synthesis of lipophilic triphosphate prodrugs of abacavir, carbovir, and their 1′,2′-cis-substituted carbocyclic analogues. The 1′,2′-cis-carbocyclic nucleosides were prepared by starting from enantiomerically pure (1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol by a microwave-assisted Mitsunobu-type reaction with 2-amino-6-chloropurine. All four nucleoside analogues were prepared from their 2-amino-6-chloropurine precursors. The nucleosides were converted into their corresponding nucleoside triphosphate prodrugs (TriPPPro approach) by application of the H-phosphonate route. The TriPPPro compounds were hydrolyzed in different media, in which the formation of nucleoside triphosphates was proven. While the TriPPPro compounds of abacavir and carbovir showed increased antiviral activity over their parent nucleoside, the TriPPPro compounds of the 1′,2′-cis-substituted analogues as well as their parent nucleosides proved to be inactive against HIV.

PROCESS FOR THE PREPARATION OF AMINO ALCOHOL DERIVATIVES OR SALTS THEREOF

The present invention relates to a process for the preparation of amino alcohol derivatives or salts thereof. In particular the present invention relates to process for the preparation of amino alcohol derivatives or salts thereof which may be used as intermediates in the preparation of HIV reverse transcriptase inhibitors, more preferably Carbovir and Abacavir. The present invention more specifically relates to a process for the preparation of (1S,4R)-4-amino-2-cyclopentene-1-methanol of Formula IIIa. The present invention also specifically relates to process for the preparation of Abacavir sulfate of Formula II using compound of Formula IIIa prepared according to the process of the present invention.

Enantioselective synthesis of the carbocyclic nucleoside (-)-abacavir

An enantiopure β-lactam with a suitably disposed electron withdrawing group on nitrogen, participated in a π-allylpalladium mediated reaction with 2,6-dichloropurine tetrabutylammonium salt to afford an advanced cis-1,4-substituted cyclopentenoid with both high regio- and stereoselectivity. This advanced intermediate was successfully manipulated to the total synthesis of (-)-Abacavir.