Crystalline ribofuranosyl halides and other derivatives and methods for producing same
US4282349A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Oct 16, 1978 |
| Grant date | Aug 4, 1981 |
| Priority date | — |
| Expiry date | Oct 16, 1998 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H15/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Methyl-D-ribofuranoside is p-nitrobenzoylated to yield crystalline methyl 2,3,5-tri-O-(p-nitrobenzoyl)-.beta.-D-ribofuranoside which can be used to prepare a stable, crystalline 2,3,5-tri-O-(p-nitrobenzoyl)-.beta.-D-ribofuranosyl bromide which in turn is useful as a precursor of natural or synthetic purine and pyrimidine nucleosides, as well as of glycosides. This bromide can also be cyanated to yield crystalline 2,5-anhydro-3,4,6-tri-O-(p-nitrobenzoyl)-D-allononitrile which in turn can be hydrolyzed and subsequently reacted with polyamino pyrimidines to yield nucleoside analogs such as 8-.beta.-D-ribofuranosyl adenine. This bromide also can by hydrolyzed to yield crystalline 2,3,5-tri-O-(p-nitrobenzoyl)-D-ribofuranose which in turn can be p-nitrobenzolated to yield crystalline 1,2,3,5-tetra-O-(p-nitrobenzoyl)-.beta.-D-ribofuranose. This latter compound can be brominated to produce an alphabromide derivative which is useful as a precursor of nucleosides.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.