1990
DOI: 10.1021/ja00171a021
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Sulfonamidoglycosylation of glycals. A route to oligosaccharides with 2-aminohexose subunits

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Cited by 201 publications
(80 citation statements)
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“…Aminohalogenation of α,β-unsaturated carbonyl substrates has become an attractive tool for the synthesis of these functional 1,2-haloamines in tandem carbon-nitrogen and carbon-halogen bond formations [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. To date, several new aminohalogenation processes have been developed with many kinds of nitrogen/halogen sources, such as N,N-dichloro-2-nitrobenzenesulfonamide [3,[20][21][22], N,N-dichloro-ptoluene-sulfonamide [23][24][25][26][27][28], N,N-dichlorobenzenesulfonamide [11,[29][30], N,N-dibromo-p-toluenesulfonamide [31][32][33][34][35], N,N-dibromo-benzenesulfonamide [36][37][38] and chloramine-T [39][40][41] in the presence of numerous catalysts. α,β-Unsaturated carbonyl substrates used for this reaction include α,β-unsaturated carboxylic esters [25,26], α,β-unsaturated ketones [42,43], methylenecyclopropanes …”
Section: Introductionmentioning
confidence: 99%
“…Aminohalogenation of α,β-unsaturated carbonyl substrates has become an attractive tool for the synthesis of these functional 1,2-haloamines in tandem carbon-nitrogen and carbon-halogen bond formations [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. To date, several new aminohalogenation processes have been developed with many kinds of nitrogen/halogen sources, such as N,N-dichloro-2-nitrobenzenesulfonamide [3,[20][21][22], N,N-dichloro-ptoluene-sulfonamide [23][24][25][26][27][28], N,N-dichlorobenzenesulfonamide [11,[29][30], N,N-dibromo-p-toluenesulfonamide [31][32][33][34][35], N,N-dibromo-benzenesulfonamide [36][37][38] and chloramine-T [39][40][41] in the presence of numerous catalysts. α,β-Unsaturated carbonyl substrates used for this reaction include α,β-unsaturated carboxylic esters [25,26], α,β-unsaturated ketones [42,43], methylenecyclopropanes …”
Section: Introductionmentioning
confidence: 99%
“…The two most exploited synthetic channels to D-GalNAc and its derivatives are those based (a) on the C-4 epimerization of the largely and cheaply available 7 mimicking thus the biosynthetic pathway, and (b) on the amination at C-2 of D-galactose with formal retention of configuration. [8][9][10][11] The first D-Gal to D-GalNAc transformation was described in 1976 8 by Paulsen and co-workers using as key reaction the sodium azide opening of the epoxide ring of the In the frame of a general project on the synthesis of β-D-hexosaminyl-(1→4)-D-Glcp disaccharides, 14 we considered the synthesis of β-D-GalNAcp-(1→4)-D-Glcp (1a), a natural disaccharide present in minute amount in the bovine colostrum. 15 The sole reported synthesis of 1a is based on an enzymatic glycosylation involving a β-1→4-N-acetylgalactosaminyltransferase.…”
Section: Introductionmentioning
confidence: 99%
“…[4,5] Clearly, a direct glycosidation method by using donors with the natural N-acetyl function would constitute an ideal procedure in terms of efficiency and practicality. In practice, however, the reaction of these donors, 1, generally leads to the predominant formation of oxazoline derivatives 3 through neighboring-group participation and the subsequent abstraction of a proton from the NH group (Scheme 1).…”
mentioning
confidence: 99%