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 yielded 6-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl][1,2,4]-triazolo[1,5-a]pyrimidine (5).
Bari
Ahmed
A
Institut für Chemie der Universität Rostock, D-18051 Rostock, Germany.
Feist
Holger
H
Michalik
Manfred
M
Peseke
Klaus
K
D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
C525036:3,4-di-O-benzyl-2-formylarabinal; D011741:Pyrimidine Nucleosides; D001089:Arabinose