136522-33-3

Basic information

• Product Name: (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-Cyclopentene-1- methanol
• Synonyms: (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-Cyclopentene-1- methanol;((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol
• CAS NO: 136522-33-3
• Molecular Formula: C₁₁H₁₂ClN₅O
• Molecular Weight: 266
• EINECS: 1308068-626-2
• Mol File: 136522-33-3.mol

Chemical Properties

• Melting Point: 208℃
• Boiling Point: 572.0±60.0 °C(Predicted)
• Appearance: /
• Density: 1.74
• Storage Temp.: 2-8°C
• PKA: 14.86±0.10(Predicted)
• CAS DataBase Reference: (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-Cyclopentene-1- methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-Cyclopentene-1- methanol(136522-33-3)
• EPA Substance Registry System: (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-Cyclopentene-1- methanol(136522-33-3)

Safety Data

• Hazardous Substances Data: 136522-33-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-Cyclopentene-1-methanol is used as a research compound for exploring its potential biological activity and therapeutic applications. The presence of the purine group suggests that it may interact with various biological targets, making it a candidate for the development of new drugs.
Used in Drug Development:
In the pharmaceutical industry, (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-Cyclopentene-1-methanol is used as a lead compound for the design and synthesis of novel therapeutic agents. Its unique structure and functional groups provide opportunities for further chemical modifications to optimize its pharmacological properties, such as potency, selectivity, and bioavailability.

Upstream product

• 172015-79-1 ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride 
• 1026616-09-0 6-chloro-9-((1R,4S)-4-((triisopropylsilyloxy)methyl)cyclopent-2-enyl)-9H-purin-2-amine 
• 141271-13-8 (1S,4R)-4-(<2'-amino-6'-chloro-5'-<(4''-chlorophenyl)azo>pyrimidin-4'-yl>amino)cyclopent-2-enylmethanol 
• 122-51-0 orthoformic acid triethyl ester 
• 141271-12-7 (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 
• 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 
• 141271-11-6 (-)-(1S,4R)-4-<(2'-amino-6'-chloropyrimidin-4'-yl)amino>-cyclopent-2-enylmethanol 
• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 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 
• 159418-19-6 (4aR,7S,7aS)-hexahydro-7-iodocyclopenta<1,3>dioxin-2-one 
• 67886-26-4 (S)-(-)-3-(hydroxymethyl)-cyclopent-1-ene 

Downstream Products

• 136470-78-5 abacavir 
• 124752-25-6 (1α,4α)-4-(2,6-Diamino-9H-purin-9-yl)-2-cyclopentenyl-carbinol 

Relevant articles and documents

An asymmetric synthesis of (-)-carbovir

Enantioselective deprotonation of trans-4-t-butyldimethylsiloxymetyl-1,2-epoxycyclopentane (trans-4) by a chiral lithium amide, lithium (S)-2-(pyrrolidin-1-ylmethyl)pyrrolidide (1), afforded (1S,4S)-trans-4-t-butyldimethylsiloxymethyl-2-cyclopenten-1-ol (trans-7) in 83% ee. Alcohol trans-7 was easily transformed to (-)-carbovir, an anti-HIV carbocyclic nucleoside.

ANTIVIRAL 4-(2-AMINO-6-HETEROCYLYL-9H-PURIN-9-YL)-2-CYCLOPENTENE-1 -METHANOL COMPOUNDS

The present invention relates to certain antiviral compounds of formula I as defined herein that function as nucleoside reverse transcriptase inhibitors. The present invention also relates to processes for the preparation of these compounds, pharmaceutical compositions comprising them and to their use for the treatment of retroviral infections, and in particular their use in the treatment of HIV-1 virus.

Novel salts of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol

The present invention relates to novel salts of (1S,4R)-cis-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1 -methanol of Formula I or solvates or hydrates thereof, wherein M represents hemimalonate, malonate, hemioxalate, oxalate, hydrobromide, dihydrobromide, hemimaleate, maleate.

Enantioselective syntheses of carbanucleosides from the Pauson-Khand adduct of trimethylsilylacetylene and norbornadiene

(Chemical Equation Presented) A new enantioselective approach to carbanucleosides from Pauson-Khand (PK) adduct 1 is disclosed. The chiral cyclopentenone 1 is readily accessible in enantiomerically pure form via PK reaction of trimethylsilylacetylene and norbornadiene using N-benzyl-N- diphenylphosphino-tert-butyl-sulfinamide as a chiral P,S ligand. (-)-Carbavir and (-)-Abacavir were enantioselectively synthesized starting from (-)-1. The key steps of the sequence are a photochemical conjugate addition of a hydroxymethyl radical, a retro-Diels-Alder reaction, and a palladium catalyzed allylic substitution to introduce the nucleobase.

PROCESS FOR THE PREPARATION OF (1S, 4R) -CIS-4-‘2-AMINO-6CHLORO-9H-PURIN-9-YL!-2-CYCLOPENTENE-1-METHANOL

A process for preparing a chloropurine compound of formula (I) or a derivative thereof, which comprises ring closure of the compound of formula (VII) or a derivative thereof in the presence of catalytic acid and at least one equivalent of a formate derivative.

Therapeutic nucleosides

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

An efficient, general asymmetric synthesis of carbocyclic nucleosides: Application of an asymmetric aldol/ring-closing metathesis strategy

A general and efficient synthesis of carbocyclic and hexenopyranosyl nucleosides has been developed. The strategy combines three key transformations: an asymmetric aldol addition to establish the relative and absolute configuration of the pseudosugar, a ring-closing metathesis to construct the pseudosugar ring, and a Trost-type palladium(0)-mediated substitution to assemble the pseudosugar and the aromatic base. Carbovir, abacavir, and their 2'-methyl derivatives as well as hexenopyranosyl nucleoside analogues have been prepared by this sequence.

Solid-phase synthesis of carbocyclic nucleosides.

[formula: see text] An efficient solid-phase synthesis of carbocyclic nucleosides has been developed. The key step is the palladium-catalyzed coupling of a purine derivative to a resin-bound allylic benzoate. The resulting products may be further functionalized on the solid phase. Acidic cleavage affords carbocyclic nucleosides, a class of compounds with demonstrated biological activity and substantial current interest.

Practical enantiodivergent syntheses of both enantiomers of carbovir, 1592U89 and six-membered ring analogues

The hydroxylactones 4a-b (both available in optically pure form from biocatalytic processes) have been used in the preparation of carbovir, 1592U89, and their six-membered ring analogues.