Protection of nucleosides
US7002006B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Feb 12, 2003 |
| Grant date | Feb 21, 2006 |
| Priority date | — |
| Expiry date | Sep 1, 2023 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H19/048
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process of manufacturing protected nucleosides comprises reacting a nucleoside with a protecting reagent in the presence of a regioselective activator to produce a regioselectively protected nucleoside. In some embodiments of the inventive method, an optionally substituted trityl or optionally substituted pixyl group is selectively added to the 5′-O-position of a nucleoside in the presence of lutidine as activator or activator/solvent. The inventive method results in improved selectivity of the 5′-O-position over the 3′-O-position, thereby improving overall product yield and purity, and permitting simplified purification protocols, in some cases obviating the need for chromatography to produce a purified protected nucleoside suitable for automated synthesis of oligonucleotides, such as primers, probes and antisense molecules.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.