摘要 |
Heavily fluorinated sugar analogs of formulawhereinR1 is selected from alkyl, alkenyl, aryl, -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,whereinR3 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; andwherein 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.
|