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Updated: Sep 25, 2025

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Ferrocenium complex aided O-glycosylation of glycosyl halides

Deva Saroja Talasila¹, Eike B Bauer¹

¹University of Missouri - St. Louis, Department of Chemistry and Biochemistry, One University Boulevard St. Louis MO 63121 USA bauere@umsl.edu +1 314 516 5342 +1 314 516 5311.

|May 2, 2022

Abstract:

A new strategy for the activation of glycosyl halide donors to be utilized in glycosylation reactions is presented, utilizing the ferrocenium (Fc) complexes [FcB(OH)₂]SbF₆ and FcBF₄ as promoters. The scope of the new system has been investigated using glycosyl chloride and glycosyl fluoride donors in combination with common glycosyl acceptors, such as protected glucose. The corresponding glycosylation products were formed in 95 to 10% isolated yields with α/β ratios ranging from 1/1 to β only (2 to 14 h reaction time at room temperature, 40 to 100% ferrocenium promoter load).

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