892409-72-2

Upstream product

• 4330-20-5 N-3-benzoylthymine 
• 648414-60-2 (1R,2S,3S)-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol 
• 191480-69-0 (3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene 
• 110567-21-0 (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

Synthesis of Enantiomerically Pure 1′,2′- cis - Dideoxy, - dideoxydidehydro, - Ribo and - Deoxy Carbocyclic Nucleoside Analogues

We describe a short and stereospecific synthesis of different series of 1′,2′- cis -disubstituted carbocyclic nucleoside analogues. All-natural nucleobases or their precursors are coupled in a microwave-assisted Mitsunobu-type reaction with enantiomerically pure (1 R,2 S)-2-(benzyloxymethyl)cyclopent-3-enol. By modifying the cyclopentene scaffold, our synthetic strategy gives access to a series of 1′,2′- cis -disubstituted carbocyclic nucleoside analogues of the dideoxy (dd), dideoxydidehydro (d 4) or the ribo series. The ribo series is synthesized in a more convenient way compared to a previous route. The deoxy series of 1′,2′- cis -disubstituted carbocyclic nucleoside analogues is prepared following an earlier reported approach. This synthesis involves the microwave-assisted coupling of (1 R,2 S,3 S)-3-(benzyloxy)-2-[(benzyloxy)methyl]cyclopentan-1-ol with the appropriate nucleobases.

Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs

A new divergent approach towards carbocyclic α-, iso- and 3′-epi-nucleosides starting from enantiomerically pure (1S,2R)-2-benzyloxymethylcyclopent-3-enol (5) is described. In the key step, isomeric cyclopentanols were condensed with a N3-protected pyrimi