120443-30-3

Upstream product

• 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 
• 144363-98-4 cis-5-dimethylthexylsilyloxymethyl-2-cyclopentenol 
• 140139-15-7 5-(dimethylthexylsilyloxymethyl)cyclopentanone 
• 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 
• 144363-97-3 5-dimethylthexylsilyloxymethyl-2-cyclopentenone 
• 10310-21-1 2-Amino-6-chloropurin 
• 25125-21-7 4-(hydroxymethyl)cyclopentene 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 542-92-7 cyclopenta-1,3-diene 
• 109000-07-9 2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 124575-13-9 cis-4-p-toluenesulfonylaminocyclopent-2-enylmethanol 

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 academic research and scientific papers

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.

π-Allylpalladium formation from allylic amines via N,N-ditosylimides and N-tosylamides: Efficient synthesis of the antiviral agent carbovir

Allylic amines can be easily converted into their N,N-ditosylimides or N-tosylamides which are sufficiently good leaving groups to afford π-allylpalladium complexes and, hence, with nucleophiles, new allylic systems with retention of configuration. The synthetic utility of this process has been demonstrated by an efficient synthesis of the antiviral agent (±)-carbovir (1) from cyclopentadiene in only seven steps and 13% overall yield.

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.

New efficient method for the synthesis of the antiviral agent carbovir

An efficient synthesis of (±)-carbovir 1 and simple des(hydroxymethyl) analogues, e.g., 5, is reported which uses a new approach for attaching nucleoside bases to cycloalkene systems.

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.