Pyrimidine acyclo-C-nucleosides by ring transformations of 2-formyl-L-arabinal

The protected 2-formyl-L-arabinal 2 reacted with thiourea and cyanamide in the presence of sodium hydride to afford via ring transformations the 5-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyrimidines 3 and 4, respectively. Similarly, treatment of 2 with 3-amino-2H-1,2,4-triazole yielde...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2005-08, Vol.10 (8), p.837-842
Hauptverfasser:	Bari, Ahmed, Feist, Holger, Michalik, Manfred, Peseke, Klaus
Format:	Artikel
Sprache:	eng
Schlagworte:	Arabinose - analogs & derivatives Arabinose - chemistry Carbon fused pyrimidines Glycals Magnetic Resonance Spectroscopy nucleoside analogues push-pull alkenes Pyrimidine Nucleosides - chemical synthesis Pyrimidine Nucleosides - chemistry pyrimidines ring transformation Sodium Spectrum analysis
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Beschreibung
Zusammenfassung:	The protected 2-formyl-L-arabinal 2 reacted with thiourea and cyanamide in the presence of sodium hydride to afford via ring transformations the 5-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyrimidines 3 and 4, respectively. Similarly, treatment of 2 with 3-amino-2H-1,2,4-triazole yielded 6-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl][1,2,4]-triazolo[1,5-a]pyrimidine (5).
ISSN:	1420-3049 1420-3049
DOI:	10.3390/10080837