Sato S, Kumazawa T, Matsuba S, Onodera J, Aoyama M, Obara H, Kamada H
Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata 992-8510, Japan.
Carbohydr Res. 2001 Aug 30;334(3):215-22. doi: 10.1016/s0008-6215(01)00184-7.
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 (BF(3) x OEt(2)) and an amine base afforded the corresponding hydroxylamine-O-glycosides in 25-100% yields.
