215445-56-0Relevant articles and documents
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 (1998)
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).