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  • Glycosylation of sialyl acetates with a novel catalyst combination: bismuth triflate and BF3.OEt2 system.

Glycosylation of sialyl acetates with a novel catalyst combination: bismuth triflate and BF3.OEt2 system.

Bioorganic & medicinal chemistry (2003-06-24)
Kiyoshi Ikeda, Yasuhiro Torisawa, Takao Nishi, Junichi Minamikawa, Kiyoshi Tanaka, Masayuki Sato
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Boron trifluoride diethyl etherate, for synthesis
Sigma-Aldrich
Boron trifluoride diethyl etherate, purified by redistillation, ≥46.5% BF3 basis