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

Ahmed Bari; Holger Feist; Manfred Michalik; Klaus Peseke

doi:10.3390/10080837

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

Molecules. 2005 Aug 31;10(8):837-42. doi: 10.3390/10080837.

Authors

Ahmed Bari¹, Holger Feist, Manfred Michalik, Klaus Peseke

Affiliation

¹ Institut für Chemie der Universität Rostock, D-18051 Rostock, Germany.

Abstract

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Arabinose / analogs & derivatives*
Arabinose / chemistry
Magnetic Resonance Spectroscopy
Pyrimidine Nucleosides / chemical synthesis*
Pyrimidine Nucleosides / chemistry

Substances

3,4-di-O-benzyl-2-formylarabinal
Pyrimidine Nucleosides
Arabinose