Synthesis of 3′-fluoro-4′-amino-hexitol nucleosides with a pyrimidine nucleobase as building blocks for oligonucleotides

Jabgunde, Amit M; Patil, Rahul S; De, Swarup; Lescrinier, Eveline; De Jonghe, Steven; Beigelman, Leonid; Herdewijn, Piet

doi:10.1016/j.tet.2019.01.026

Synthesis of 3′-fluoro-4′-amino-hexitol nucleosides with a pyrimidine nucleobase as building blocks for oligonucleotides

Author:

Jabgunde, Amit M

Patil, Rahul S ; De, Swarup ; Lescrinier, Eveline ; De Jonghe, Steven ; Beigelman, Leonid ; Herdewijn, Piet

Keywords:

Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, Hexitol nucleoside, Oligonucleotide, Uracil, Cytidine, TELOMERASE TEMPLATE ANTAGONIST, D-ALTRITOL NUCLEOSIDES, INHIBITION, BASE, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3101 Biochemistry and cell biology, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

© 2019 Elsevier Ltd The synthesis of 3′-fluoro-4′-amino-hexitol nucleosides with a uracil and cytosine nucleobase was performed. The synthesis started from 1,5:2,3-dianhydro-4,6-benzylidene-allitol and afforded the target compounds in 15 steps. These protected hexitol nucleosides are valuable building blocks for the preparation of a new class of oligonucleotides.