Propargyl modified nucleosides and nucleotides
US5744595A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jul 25, 1995 |
| Grant date | Apr 28, 1998 |
| Priority date | — |
| Expiry date | Jul 25, 2015 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H21/00
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention describes a novel 2'-O-alkylation reaction to produce a novel series of nucleosides carrying the 2'-O-propargyl group, using propargyl bromide, dibutyl tin oxide and tetrabutyl ammonium bromide. The procedure involves novel techniques for regioselective introduction of 2'-/3'-O-propargyl group directly on the 5'-DMT-N-protected- nucleosides using dibutyl tin oxide as a mild base in conjunction with a phase transfer catalyst, tetrabutyl ammonium bromide. The reaction process has many significant features and leads to isomeric ratios in favor of the 2'-regio isomer. This allows the synthesis of the corresponding phosphoramidites of high purity.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.