Heavily fluorinated sugar analogs
US6013790A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Sep 25, 1997 |
| Grant date | Jan 11, 2000 |
| Priority date | — |
| Expiry date | Sep 25, 2017 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H19/16
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Heavily fluorinated sugar analogs of formula ##STR1## wherein R.sub.1 is selected from alkyl, alkenyl, aryl, CH.sub.2 OH, --CH.sub.2 --O-alkyl, --CH.sub.2 --O-aryl, --CH.sub.2 OPO.sub.3 H, --CH.sub.2 --O-carbohydrate, --CH.sub.2 --NH-peptide, or --CH.sub.2 --O-peptide; PA1 wherein R.sub.2 is selected from hydroxy, --O-carbohydrate, --NH-peptide, ##STR2## wherein R.sub.3 is selected from H, halogen, lower alkyl, lower alkenyl, lower haloalkyl, lower haloalkenyl, amino, mono- or di-lower alkylamino; PA2 wherein R.sub.4 is selected from amino, hydroxy, alkoxy, or halogen; and PA2 wherein R.sub.5 is H or amino. The compounds of formula (I) are useful as antiviral and antineoplastic agents and the compounds of formula (II) are useful as plant growth inhibitors and herbicides. Also disclosed is a method for preparing the heavily fluorinated sugars of the present invention which utilizes inexpensive starting materials which incorporate the desired number of fluorine moieties and a new reagent, benzyloxymethylzinc bromide, for introducing the 5'-hydroxymethyl moiety. The synthetic method of the present invention is advantageous in that it does not require late stage fluorination step.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.