Novel glycosylation of the nitroxyl radicals with peracetylated glycosyl fluorides using a combination of BF(3) x OEt(2) and an amine base as promoters.
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.
Sato
S
S
Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata 992-8510, Japan. tj419@dip.yz.yamagata-u.ac.jp
Kumazawa
T
T
Matsuba
S
S
Onodera
J
J
Aoyama
M
M
Obara
H
H
Kamada
H
H
D000588:Amines / Q000737:chemistry; D000975:Antioxidants / Q000737:chemistry; D001880:Boranes / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D011837:Radiation-Protective Agents / Q000737:chemistry; D013113:Spin Labels / Q000138:chemical synthesis*
D000588:Amines; D000975:Antioxidants; D001880:Boranes; D003497:Cyclic N-Oxides; D005609:Free Radicals; D006027:Glycosides; D009589:Nitrogen Oxides; D011759:Pyrrolidines; D011837:Radiation-Protective Agents; D013113:Spin Labels; C077426:3-carbamoyl-2,2,5,5-tetramethyl-1-pyrrolidinyl-N-oxyl; C039900:nitroxyl; D005459:Fluorides