Glycosylation of sialyl acetates with a novel catalyst combination: bismuth triflate and BF3.OEt2 system.
A combined system of bismuth triflate [Bi(OTf)(3)] and boron trifluoride etherate (BF(3).OEt(2)) in dichloromethane is an efficient promoter for the glycosylation of N-acetylneuraminic acid derivatives. The co-existence of two acid catalysts such as Bi(OTf)(3)-BF(3).OEt(2) or Bi(OTf)(3)-PPA is confirmed to be essential for obtaining high yields of glycosylation products with p-nitrobenzyl alcohol, which also turned to be superior to those reported previously.
Ikeda
Kiyoshi
K
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, 422-8526, Shizuoka, Japan. ikeda@ys2.u-shizuoka-ken.ac.jp
Torisawa
Yasuhiro
Y
Nishi
Takao
T
Minamikawa
Junichi
J
Tanaka
Kiyoshi
K
Sato
Masayuki
M
D000085:Acetates / Q000737:chemistry*; D019905:Benzyl Alcohol / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D008698:Mesylates / Q000737:chemistry*; D008956:Models, Chemical; D009574:Nitro Compounds / Q000737:chemistry; D012794:Sialic Acids / Q000737:chemistry*; D012997:Solvents; D013696:Temperature
D000085:Acetates; D001880:Boranes; D006027:Glycosides; D008698:Mesylates; D009574:Nitro Compounds; D012794:Sialic Acids; D012997:Solvents; C101707:boron trifluoride etherate; C445789:Bi(OTf)3; D019905:Benzyl Alcohol