203383-41-9Relevant academic research and scientific papers
Synthesis of 3'-C-branched 1',5'-anhydromannitol nucleosides as new antiherpes agents
Hossain, Nafizal,Van Halbeek, Herman,De Clercq, Erik,Herdewijn, Piet
, p. 2209 - 2226 (2007/10/03)
A series of 3'-β-C-branched anhydromannitol nucleosides were conveniently synthesized starting from commercially available D-ribose. The reaction sequences were: (i) conversion of the protected pentofluranose to the corresponding nitrohexopyranose; (ii) addition of the conjugated base of the nitrosugar to formaldehyde; (iii) removal of the nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to introduce the nucleobase. The conformation of intermediates and final compounds were deduced from NMR analysis. The thymine congener showed potent activity against herpes simplex virus (HSV).
Facile synthesis of 3'-C-branched 1,5-anhydrohexitol nucleosides
Hossain, Nafizal,Herdewijn, Piet
, p. 1781 - 1786 (2007/10/03)
The 3'-β-C-branched anhydrohexitol nucleosides have been conveniently synthesised starting from commercially available D-ribose following the reaction sequence: (i) conversion of protected pentofuranose sugar to the corresponding hexopyranosyl nitrosugar (ii) addition of the conjugate base of nitrosugar to formaldehyde to obtain C-branched nitro sugar (iii) removal of nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to build up the nucleobase.
