Method for the synthesis of 2′,3′-dideoxy-2′,3′-didehydronucleosides
US6927291B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Mar 1, 2002 |
| Grant date | Aug 9, 2005 |
| Priority date | — |
| Expiry date | Jun 18, 2022 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H19/16
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
An efficient synthetic route to antiviral 2′,3′-dideoxy-2′,3′-didehydro-nucleosides, such as 2′,3′-dideoxy and 2′- or 3′-deoxyribo-nucleoside analogs, from available precursors is disclosed, with the option of introducing functionality as needed. In one embodiment, a method for the preparation of β-D and β-L-2′,3′-dideoxy-2′,3′-didehydro-nucleosides is described that includes: activating a compound of structure (1) wherein B is a pyrimidine or purine base and Y is O, S or CH2 with an acyl halide of the formula X—C(═O)R1, X—C(═O)C(R1)2OC(═O)R1 or X—C(═O)OR1 (wherein X is a halogen, and each R1 is independently hydrogen, lower alkyl, alkyl, aryl or phenyl); reducing the resulting compound with a reducing agent to form a 2′,3′-dideoxy-2′,3′-didehydro-nucleoside; and optionally deprotecting the nucleoside. The haloacylation of the first step can form the 2′-acyl-3′-halonucleoside, the 3′-acyl-2′-halonucleoside, or a mixture thereof.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.