2-TRIFLUOROACETAMIDO-2-DEOXY-BETA-D-GALACTOPYRANOSYL FLUORIDE AS A NEW GLYCOSYLATING AGENT IN THE SYNTHESIS OF CHROMOGENIC AND FLUOROGENIC SUBSTRATES OF ALPHA-N-ACETYLGALACTOSAMINIDASES AND BETA-N-ACETYLGALACTOSAMINIDASES

2-Trifluoroacetamido-2-deoxy-beta-D-galactopyranosyl fluoride has been prepared in 50% yield by the four-step synthesis with the use of ethyl trifluoroacetate as N-trifluoroacetylating reagent. Reactions of this fluoride with trimethylsilyl ethers of p-nitrophenole, 4-methyl-, and 4-trifluoromethylumbelliferone followed by removal of O-substituents and modification of N-protecting groups are proposed for synthesis of N-acetyl-galactosaminidase substrates. Anomeric paris of N-trifluoroacetyl glycosides produced with the overall yield 51-67% have been easily separated by column chromatography, alpha-anomers being isolated with 17-20% yields. The structures of the previously underscribed substances are confirmed by C-13 NMR spectroscopy.