HEAVILY FLUORINATED SUGAR ANALOGS

Authors

Stephen G. Dimagno, Lincoln, NEFollow

Date of this Version

2000

Citation

Patent Number: 6,013,790

Comments

Appl. No.: 08/937,672

Abstract

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.