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Koenigs–Knorr reaction
About: Koenigs–Knorr reaction is a research topic. Over the lifetime, 106 publications have been published within this topic receiving 4521 citations.
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TL;DR: IF5-pyridine-HF, an air- and moisture-stable fluorinating reagent, was applied to the synthesis of glycosyl fluorides from (phenylthio)glycosides and common protecting groups of alcohol and diol can tolerate the reaction conditions performed.
5 citations
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TL;DR: The present method would be useful for the block synthesis of glycosyl donors in the total synthesis of blanched oligosaccharides, especially when N-acetylglucosamines are presented at the non-reducing ends.
Abstract: A glycosylation reaction was performed using a combination of thioglycoside and glycosyl sulfoxide, which were prepared with odorless p-octyloxybenzenethiol, as a glycosyl donor and an acceptor, respectively. Promising results were obtained when p-octyloxylphenyl N-phthaloyl-D-thio-glucosaminide was activated with N-iodosuccinimide (NIS) and triflic acid (TfOH) for glycosylation of the hydroxyl group of the C-6 position of derivatives of D-glucosyl sulfoxide. Successive reduction of the resulting disaccharyl sulfoxides provided the corresponding thioglycosides, which could be used as the glycosyl donors in another glycosylation reaction to afford trisaccharides in good yield. The present method would be useful for the block synthesis of glycosyl donors in the total synthesis of blanched oligosaccharides, especially when N-acetylglucosamines are presented at the non-reducing ends.
5 citations
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TL;DR: In this article, 6-O-(4-O-Methyl-β-D-glucopyranosyl)-D-galactose has been synthesized by a Koenigs-Knorr reaction.
Abstract: 6-O-(4-O-Methyl-β-D-glucopyranosyl)-D-galactose has been synthesized by a Koenigs–Knorr reaction. The disaccharide is most readily characterized in the form of the crystalline glycosyl alditol pera...
5 citations
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TL;DR: In this paper, the influence of several crown ethers, cryptands and supported ligands on the performance of alcohols with tetra- o -acetylbromoglucose in the presence of silver nitrate was examined.
5 citations
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TL;DR: Barluenga's reagent, bis(pyridinium)iodon, was used to transform n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) into glycosyl fluorides as discussed by the authors.
Abstract: n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga’s reagent, bis(pyridinium)iodon...
4 citations