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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: In this paper, reactions of glycosyl isothiocyanates with diamines such as o-phenylenediamine, 2, 3-diaminopyridine or 5, 6-dimethyluracil gave the corresponding glycoly thioureides in good yields.
Abstract: Reactions of glycosyl isothiocyanates (1a, b, c) with diamines such as o-phenylenediamine, 2, 3-diaminopyridine or 5, 6-diamino-1, 3-dimethyluracil gave the corresponding glycosyl thioureides in good yields. Glycosyl thioureides were converted into N-glycosylaminobenzimidazoles (5a, b, c), N-glycosyl-3-deazapurine (6a) or N-glycosylaminotheophyllines (7a, b, c) in excellent yields through a cyclodesulfurization reaction.
10 citations
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TL;DR: 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate.
Abstract: A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good.
10 citations
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TL;DR: In this paper, the 13.2-O-GA29β-D-glucopyranoside (1e) and 13.1-OGA29 β-Dglocopyr-anoside(1h) were synthesized from GA29 methyl ester and confirmed by 1H NMR and GC-MS.
10 citations
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TL;DR: An improved practical synthesis of L-vancosamine-related glycosyl donors is described, and their reactivities in the aryl C-glycoside formation were compared.
Abstract: An improved practical synthesis of L-vancosamine-related glycosyl donors is described. The key steps include (1) stereoselective addition of methylcerium reagent to oximino ether and (2) stereoselective hydrogenation of exocyclic unsaturated glycoside in the presence of Wilkinson catalyst with C(5) inversion to give L-vancosamine derivatives. Three glycosyl donors were prepared, and their reactivities in the aryl C-glycoside formation were compared. Conversion of primary amine and azide to the corresponding N,N-dimethyl derivative is also described.
10 citations
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TL;DR: Glycosyl sulfates are easily synthesised from tetrabenzyl pyranoses; their reaction with various acceptors promoted by Lewis acids affords glycosides and disaccharides as α,β mixtures as mentioned in this paper.
9 citations