Novel Glycosylation of the Nitroxyl Radicals with Peracetylated Glycosyl Fluorides Using a Combination of BF3×OEt2 and an Amine Base as Promoters.

Abstract Glycosylation of the nitroxyl radicals, 4-acetoxy-2,2,6,6-tetramethylpiperidin-1-oxyl (4-acetoxy-TEMPO) and 3-carbamoyl-2,2,5,5-tetramethylpyrollin-1-oxyl (3-carbamoyl-PROXYL) with peracetylglycosyl fluoride as the glycosyl donor, in the presence of boron trifluoride diethyl etherate (BF3·OEt2) and an amine base afforded the corresponding hydroxylamine-O-glycosides in 25–100% yields.