141271-11-6

Basic information

• Product Name: (1S,4R)-4-[(2,5-DiaMino-6-chloro-4-pyriMidinyl)aMino]-2-cyclopentene-1-Methanol
• Synonyms: (1S,4R)-4-[(2,5-DiaMino-6-chloro-4-pyriMidinyl)aMino]-2-cyclopentene-1-Methanol;(1S-cis)-4-[(2,5-DiaMino-6-chloro-4-pyriMidinyl)aMino]-2-cyclopentene-1-Methanol
• CAS NO: 141271-11-6
• Molecular Formula: C₁₀H₁₃ClN₄O
• Molecular Weight: 256
• Product Categories: Bases & Related Reagents;Impurities;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Impurities, Nucleotides, Bases & Related Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 141271-11-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,4R)-4-[(2,5-DiaMino-6-chloro-4-pyriMidinyl)aMino]-2-cyclopentene-1-Methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R)-4-[(2,5-DiaMino-6-chloro-4-pyriMidinyl)aMino]-2-cyclopentene-1-Methanol(141271-11-6)
• EPA Substance Registry System: (1S,4R)-4-[(2,5-DiaMino-6-chloro-4-pyriMidinyl)aMino]-2-cyclopentene-1-Methanol(141271-11-6)

Safety Data

• Hazardous Substances Data: 141271-11-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,4R)-4-[(2,5-DiaMino-6-chloro-4-pyriMidinyl)aMino]-2-cyclopentene-1-Methanol is used as an impurity in the production of Abacavir (A105000). Abacavir is an antiretroviral medication used to treat HIV-1 infection. The presence of this compound as an impurity is significant for ensuring the quality, safety, and efficacy of the final drug product.

Upstream product

• 56-05-3 2-Amino-4,6-dichloropyrimidine 
• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 71-36-3 butan-1-ol 
• 229613-83-6 (–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride 
• 130931-84-9 (-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 127061-46-5 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 
• 130931-86-1 (-)-(1S,4R)-4-acetamidocyclopent-2-enylmethanol 
• 182689-48-1 Acetic acid (1S,4R,5S)-4-acetoxymethyl-5-tert-butoxy-cyclopent-2-enylmethyl ester 
• 182689-56-1 Acetic acid (1S,4R,5R)-5-tert-butoxy-4-hydroxymethyl-cyclopent-2-enylmethyl ester 
• 182689-61-8 Acetic acid (1S,4S,5S)-5-tert-butoxy-4-methoxycarbonylamino-cyclopent-2-enylmethyl ester 
• 1026493-16-2 (1S,4S,5S)-4-Acetoxymethyl-5-tert-butoxy-cyclopent-2-enecarboxylic acid 
• 182689-64-1 Acetic acid (1S,4R)-4-methoxycarbonylamino-cyclopent-2-enylmethyl ester 
• 182689-66-3 ((1R,4S)-4-Hydroxymethyl-cyclopent-2-enyl)-carbamic acid methyl ester 

Downstream Products

• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 141271-12-7 (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 
• 141271-13-8 (1S,4R)-4-(<2'-amino-6'-chloro-5'-<(4''-chlorophenyl)azo>pyrimidin-4'-yl>amino)cyclopent-2-enylmethanol 

Relevant articles and documents

Therapeutic nucleosides

The present invention relates to intermediates useful for the preparation of certain compounds, for example, purine carbocyclic nucleosides.

Chemoenzymatic synthesis of antiviral carbocyclic nucleosides: Asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes using Rhizopus delemar lipase

7-Substituted norbornadienes were stereoselectively converted into the meso-3,5-bis(acetoxymethyl)cyclopentenes by a three-step sequence of ozonolysis, reduction, and acetylation. Rhizopus delemar lipase (RDL)-catalyzed asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes afforded the monoalcohols of high enantiomeric purities (> 95% ee) in good yields (64-95%). The obtained monoalcohols 11 and 14 could be applied for the synthesis of antiviral carbocyclic nucleosides (-)-carbovir and (-)-BCA.

Antiviral combination comprising nucleoside analogs

Antiviral and antitumor compositions are disclosed comprising a mixture of AZT, ribavirin, d4T or CS-87 with a compound of general formula: STR1 wherein Z is H, OH or NH2, Y is CH, and X is selected from the group consisting of H, N(R)2, SR, OR or halogen, wherein R is H, lower(C1 -C4)alkyl, aryl or mixtures thereof, and the pharmaceutically-acceptable derivatives thereof.

Potential Use of Carbocyclic Nucleosides for the Treatment of AIDS: Chemo-enzymatic Syntheses of the Enantiomers of Carbovir

The lactam (1R,4S)-2-azabicyclohept-5-en-3-one , derived by whole cell enantiospecific hydrolysis of the racemate was converted into (-)-carbovir (-)-1 in ten steps.Lipase catalysed acetylation of 4-cis-hydroxycyclopent-2-enylmethyl tripheny

6-substituted purine carbocyclic nucleosides

The present invention relates to 6-substituted purine carbocyclic nucleosides and their use in medical therapy particularly in the treatment of HIV and HBV infections. Also provided are pharmaceutical formulations and processes for the preparation of comp

Dideoxycarbocyclic nucleosides

Antiviral and antitumor compounds are disclosed of general formula: STR1 wherein Z is H, OH or NH2, Y is CH or N, the bond indicated by C1 '--C2 ' is absent or, in combination with the C1 '--C2 ' bond is the unit CH=CH, and X is selected from the group consisting of H, N(R2), SR, OR or halogen, wherein R is H, lower (C1 -C4)alkyl, aryl or mixtures thereof, and the pharmaceutically acceptable salts thereof.

Optically-active isomers of dideoxycarbocyclic nucleosides

Antiviral and antitumor compounds are disclosed of general formula: STR1 wherein Z is H, OR' or NH2, wherein R' is H, (C1 -C4)alkyl, aryl, CHO, (C1 -C16)alkanoyl or O=P(OH)2, Y is CH or N, and X is selected from the group consisting of H, N(R2), SR, OR' or halogen, wherein R is H, lower(C1 -C4)alkyl, aryl or mixtures thereof, and the pharmaceutically-acceptable salts thereof.

Antiviral nucleoside combination

Synergistic antiviral combinations of nucleoside derivatives; pharmaceutical formulations containing said combinations; use of the combinations in the treatment or prophylaxis of retroviral infections.

Guanine derivatives having antiviral activity and their pharmaceutically acceptable salts

Amino acid esters of carbovir have been found to have improved bioavailability after oral administration compared with carbovir. The esters are particularly useful for the treatment of hepatitis B virus and retrovirus (e.g. human immunodeficiency virus) infections. A preferred amino acid ester is the valine ester.