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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: Glycosyl sulfonium ions could be used as storable intermediates for reactions with various glycosyl acceptors including thioglycosides to give the corresponding disaccharides.
54 citations
TL;DR: This chapter discusses the synthesis of 1,2- trans glycosyl azides from Glycosyl halides by intramolecular rearrangement and elaborates the reduction and oxidation of glycosy azides.
Abstract: Publisher Summary This chapter discusses the synthesis and transformation of glycosyl azides. Owing to their functional group, glycosyl azides constitute important and versatile derivatives for carbohydrate chemistry. Because of the dipole character of organic azides, they can function both as nucleophiles and electrophiles and readily undergo dipolar cycloadditions. In addition, as configurationally stable groups, azides are well suited as starting materials for the formation of other nitrogen-containing functionalities such as amines, amides, ureas, carbodiimides, and others. The only method known up to 1974 for preparing glycosyl azides was from acylated glycosyl halides by the treatment with sodium or silver azide. However, because of the reactivity of glycosyl halides with water, the very low solubility of sodium azide in organic solvents, and the thermal ability of silver azide, there were considerable difficulties in preparing the corresponding glycosyl azides. This chapter discusses the synthesis of 1,2- trans glycosyl azides from glycosyl halides. It also explains the synthesis of 1,2- trans -glycopyranosyl azides by intramolecular rearrangement and elaborates the reduction and oxidation of glycosyl azides.
54 citations
TL;DR: The Koenigs-Knorr reaction of the bromide with benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α- D -glucopyranoside gave an almost stereospecific condensation, as shown by removal of protecting groups, reduction of the product to the corresponding disaccharide alcohol, and analysis of its pertrimethylsilyl) ether by gas-liquid chromatography as discussed by the authors.
53 citations
TL;DR: In this article, the preparation and application of anomeric glycosyl phosphinimides in preparative synthesis were studied, starting from the appropriate GAs and trialkyl or triaryl phosphines, the corresponding GAs were readily converted into 1- N -acyl-gluco- and galactopyranosyl amines with high yields by applying activated acid derivatives or simple carboxylic acids.
52 citations
TL;DR: Partial benzylation of methyl α-L -fucopyranoside gave the 2,4-, and 3,4-dibenzyl ethers in the ratio of 3:2, and no 2,3-isomer could be detected in the reaction mixture.
51 citations