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DOI: 10.1055/s-0031-1289688
Carbocyclic 4-Deazaformycins
Publikationsverlauf
Publikationsdatum:
06. Februar 2012 (online)

Abstract
The preparation of carbocyclic 4-deazaformycin and its 5′-homoanalogue from a common vinyl precursor, and its N-1 and N-2 methyl derivatives is reported. The syntheses began with a highly stereoselective SN2 reaction between lithio 4-picolines and a protected 2,3-dihydroxy-4-vinylcyclopentyl triflate. The requisite fused pyrazole ring was created by an intramolecular diazonium reaction that was followed by vinyl transformation into the hydroxymethyl and the hydroxyethyl groups. The N-methyl derivatives arose by standard methylation conditions and the resultant N-Me regiochemistry was assigned by homo- and heteronuclear NMR spectroscopy.
Key words
C-nucleosides - carbocyclic nucleosides - pyrazolo[3,4-c]pyridines
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References
Crystallographic data (Figure [³] ) for 25, which was a minor product in the ammonolysis of 12 have been deposited with Cambridge Crystallographic Data Centre (e mail: ccdc@code.cam.ac.uk) and allocated the deposition number CCDC 851387.

Figure 3 Hydrolyis side-product from 12