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

• 216481-88-8 (+)-cis-2-amino-6-chloro-9-<(4'R)-(hydroxymethyl)cyclopent-2'-en-(1'S)-yl>purine 
• 765-30-0 Cyclopropylamine 
• 172721-00-5 (+/-)-trans-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol 
• 268737-90-2 [4S,2R,3R]-(4-benzyl-2-thioxooxazolidin-3-yl)(2-hydroxycyclopent-3-enyl)methanone 
• 136470-88-7 (-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide 
• 172015-79-1 ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride 
• 171887-04-0 (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene 
• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 178456-36-5 ((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate 
• 61865-49-4 ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique 
• 151765-20-7 (1S,5S)-5-hydroxymethyl-2-cyclopenten-1-ol 
• 229177-44-0 (1R,cis)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol 
• 171887-02-8 2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine 
• 171887-03-9 N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide 

Relevant articles and documents

Abacavir intermediate and method for purifying same

The invention discloses an abacavir intermediate and a method for purifying the same. The method includes heating mixtures with abacavir intermediate crude products, purified water and water-soluble organic solvents until the abacavir intermediate crude products are completely dissolved so as to obtain mixed liquid; carrying out cooling and crystallization treatment on the mixed liquid; carrying out filtering and drying treatment after crystallization treatment is carried out so as to obtain abacavir intermediate pure products. A structural formula of the abacavir intermediate is shown as a formula IV. The abacavir intermediate and the method have the advantage that the method is easy and convenient to implement and is suitable for industrial production.

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.