Synthesis of 1,5-anhydro-D-mannitol nucleosides with a purine base moiety

Article abstract of DOI:10.1080/07328319808004713

D-Mannitol nucleosides with a purine base moiety have been conveniently synthesized strating from 1,5-anhydro-4,6-O-benzylidene-D-glucitol. The 3-OH function of 1,5-anhydro-4,6-O-benzylidene-D-glucitol was selectively protected with t-butyldimethylsilyl group and subsequently converted to the corresponding O-triflate derivative for the introduction of the nucleobase moietes. These nucleoside derivatives were transformed to 1,5-Anhydro-6-O- MMTr-2-(N⁶-benzoyladenin-9-yl)-2-deoxy-3-O-TBDMS-D-mannitol and 1,5-Anhydro- 6-O-MMTr-2-(N²-isobutyrylguanin-9-yl)-2-deoxy-3-O-TBDMS-D-mannitol, useful as the building blocks for oligonucleotide synthesis. Also, the synthesis of the corresponding fully deprotected anhydrohexitol nucleosides were achieved for evaluation of antiviral activity test.

Full text of DOI:10.1080/07328319808004713

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Nucleosides and Nucleotides
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Synthesis of 1,5-Anhydro-D-Mannitol
Nucleosides with a Purine Base Moeety
Nafizal Hossain a & Piet Herdewijn a
a Department of Medicinal Chemistry , Rega Institute for Medical
Research , K.U. Leuven, Minderbroedersstraat 10, B-3000, Leuven,
Belgium
Published online: 22 Aug 2006.
To cite this article: Nafizal Hossain & Piet Herdewijn (1998) Synthesis of 1,5-Anhydro-D-Mannitol
Nucleosides with a Purine Base Moeety, Nucleosides and Nucleotides, 17:9-11, 1775-1779, DOI:
10.1080/07328319808004713
To link to this article: http://dx.doi.org/10.1080/07328319808004713
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