120443-30-3

Basic information

• Product Name: 6H-Purin-6-one,2-amino-1,9-dihydro-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-
• Synonyms: 6H-Purin-6-one,2-amino-1,9-dihydro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-, (1R-cis)-; (-)-Carbovir
• CAS NO: 120443-30-3
• Molecular Formula: C₁₁H₁₃N₅O₂
• Molecular Weight: 247.2532
• Mol File: 120443-30-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 605.6°Cat760mmHg
• Flash Point: 320.1°C
• Density: 1.76g/cm³
• CAS DataBase Reference: 6H-Purin-6-one,2-amino-1,9-dihydro-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 6H-Purin-6-one,2-amino-1,9-dihydro-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-(120443-30-3)
• EPA Substance Registry System: 6H-Purin-6-one,2-amino-1,9-dihydro-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-(120443-30-3)

Safety Data

• Hazardous Substances Data: 120443-30-3(Hazardous Substances Data)

Upstream product

• 58101-60-3 methyl cyclopent-3-ene-1-carboxylate 
• 118237-87-9 cis-(+/-)-2-Amino-6-chloro-9-<4-(hydroxymethyl)-2-cyclopenten-1-yl>-9H-purine 
• 141192-85-0 cis-2-amino-9-<4-(dimethylthexylsilyloxymethyl)-2-cyclopentenyl>-6-(2-trimethylsilylethoxy)purine 
• 124575-13-9 cis-4-p-toluenesulfonylaminocyclopent-2-enylmethanol 
• 109000-07-9 2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 542-92-7 cyclopenta-1,3-diene 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 25125-21-7 4-(hydroxymethyl)cyclopentene 
• 10310-21-1 2-Amino-6-chloropurin 
• 140139-15-7 5-(dimethylthexylsilyloxymethyl)cyclopentanone 
• 144363-98-4 cis-5-dimethylthexylsilyloxymethyl-2-cyclopentenol 
• 141192-83-8 6-[2-(trimethylsilyl)ethoxy]-9H-purin-2-amine 
• 144363-96-2 5-dimethylthexylsilyloxymethyl-1-trimethylsilyloxycyclopentene 
• 141192-84-9 cis-1-acetoxy-5-dimethylthexylsilyloxymethyl-2-cyclopentene 

Downstream Products

• 138284-89-6 (1R,4S)-2-Amino-1,9-dihydro-9-<4-(hydroxymethyl)cyclopent-2-enyl>purin-6-one Triphosphate 
• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 124752-25-6 (1α,4α)-4-(2,6-Diamino-9H-purin-9-yl)-2-cyclopentenyl-carbinol 

Relevant articles and documents

Pd(0)-catalyzed allylic alkylation in the synthesis of (±)carbovir

Racemic carbovir 1 has been synthesized in 6 steps from the cyclopentanone 8 with a Pd(0)-catalyzed allylation as a key reaction.

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.

Regiochemistry and Stereochemistry in Pd(0)-Catalyzed Allylic Alkylation of Nucleoside Bases

Allylic alkylation of amino- and hydroxy-azaheterocycles, in particular nucleoside bases, has been effected using Pd(0)-catalysis.A method has been developed for the preparation of carbocyclic nucleoside analogs such as the antiviral agent Carbovir.The synthesis of an appropriately substituted cyclopentenyl acetate for this reaction is described.Carbocyclic nucleosides of thymine at N-1, of adenine at N-9 and guanine at N-9 are described.Regiochemistry and stereochemistry of the products and intermediates have been determined by NMR studies.The (trimethylsilyl)ethyl group has been found to be an excellent protecting group for the 6-OH group in guanine, and it is readily removed by fluoride ions.