Published Research - Department of Chemistry


Date of this Version



Patent Number: 6,013,790


Appl. No.: 08/937,672


Heavily fluorinated Sugar analogs of formula

wherein R1 is selected from alkyl, alkenyl, aryl, CH2OH, -CH2-O-alkyl, -CH2-O-aryl, -CH2OPO3H, -CH2-O-carbohydrate, -CH2-NH-peptide, or -CH2-O-peptide; wherein R2 is selected from hydroxy, -O-carbohydrate, -NH-peptide,

wherein R3 is selected from H, halogen, lower alkyl, lower alkenyl, lower haloalkyl, lower haloalkenyl, amino, mono- or di-lower alkylamino; wherein R4 is Selected from amino, hydroxy, alkoxy, or halogen; and wherein R5 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.