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Galway, Ireland, July 11-16, Abstract PA063
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th European Carbohydrate Symposium
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Biological roles of oligosaccharides: All of the theories are correct
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The dimethylmaleoyl group as amino protective group - Application to the synthesis of glucosamine-containing oligosaccharides
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(a) Aly, M. R. E.; Castro-Palomino, J. C.; Ibrahim, E.-S. I.; El-Ashry, E.-S. H.; Schmidt, R. R. The dimethylmaleoyl group as amino protective group - Application to the synthesis of glucosamine-containing oligosaccharides. Eur. J. Org. Chem. 1998, 2305-2316;
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Schmidt, R.R.5
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0033034714
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Synthesis of lacto-N-neotetraose and lacto-N-tetraose using the dimethylmaleoyl group as amino protective group
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(b) Aly, M. R. E.; Ibrahim, E.-S. I.; El-Ashry, E.-S. H.; Schmidt, R. R. Synthesis of lacto-N-neotetraose and lacto-N-tetraose using the dimethylmaleoyl group as amino protective group. Carbohydr. Res. 1999, 316, 121-132;
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Synthesis of lacto-N-neohexaose and lacto-N-neooctaose using the dimethylmaleoyl moiety as an amino protective group
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Aly, M. R. E.; Castro-Palomino, J. C.; Ibrahim, E.-S. L; El-Ashry, E.-S. H.; Schmidt, R. R. Synthesis of lacto-N-neohexaose and lacto-N-neooctaose using the dimethylmaleoyl moiety as an amino protective group. Eur. J. Org. Chem. 2000, 319-326.
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11
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0034728121
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N-thiodiglycoloyl derivatives of glucosamine as glycosyl donors
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Castro-Palomino, J. C.; Schmidt, R. R. N-Thiodiglycoloyl derivatives of glucosamine as glycosyl donors. Tetrahedron Lett. 2000, 41, 629-632.
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0028472595
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The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in synthesis of oligosaccharides
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(a) Blatter, G.; Beau, J.-M.; Jacquinet, J.-C. The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in synthesis of oligosaccharides. Carbohydr. Res. 1994, 260, 189-202;
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2-Deoxy-2-trichloroacetamido-D-glucopyranose derivatives in oligosaccharide synthesis: From hyaluronic acid to chondroitin 4-sulfate trisaccharides
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(b) Coutant, C.; Jacquinet, J.-C. 2-Deoxy-2-trichloroacetamido-D-glucopyranose derivatives in oligosaccharide synthesis: from hyaluronic acid to chondroitin 4-sulfate trisaccharides. J. Chem. Soc., Perkin Trans, 1, 1995, 1573-1581;
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0141512821
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Syntheses of chondroitin 4-and 6-sulfate pentasaccharide derivatives having a methyl b-D-glucopyranosiduronic acid at the reducing end
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Belot, F.; Jacquinet, J.-C. Syntheses of chondroitin 4-and 6-sulfate pentasaccharide derivatives having a methyl b-D-glucopyranosiduronic acid at the reducing end. Carbohydr. Res. 2000, 326, 88-97;
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15
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2542508127
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Unexpected stereochemical outcome of activated 4,6-0-benzylidene derivatives of the 2-deoxy-2-trichloroacetamido-D-galacto series in glycosylation reactions during the synthesis of a chondroitin 6-sulfate trisaccahride methyl glycoside
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Belot, F.; Jacquinet, J.-C. Unexpected stereochemical outcome of activated 4,6-0-benzylidene derivatives of the 2-deoxy-2-trichloroacetamido-D-galacto series in glycosylation reactions during the synthesis of a chondroitin 6-sulfate trisaccahride methyl glycoside. Carbohydr. Res. 2000, 525, 93-106.
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Glycosylation with N-troc-protected glycosyl donors
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(a) Ellervik, U.; Magnusson, G. Glycosylation with N-troc-protected glycosyl donors. Carbohydr. Res. 1996, 280, 251-260;
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17
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N-trichloroethoxycarbonyl-glucosamine derivatives as glycosyl donors
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(b) Dullenkopf, W.; Castro-Palomino, J. C.; Manzoni, L.; Schmidt, R. R. N-Trichloroethoxycarbonyl-glucosamine derivatives as glycosyl donors. Carbohydr. Res. 1996, 296, 135-147.
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18
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0014721890
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Zur synthese von 2-amino2-desoxy-a-D-glucopyranosiden
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(a) Meyer zu Reckendorf, W.; Wassiliadou-Micheli, N. Zur Synthese von 2-Amino2-desoxy-a-D-glucopyranosiden. Chem. Ber. 1970, 703, 1792-1796;
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19
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0033529841
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Stereospecific solution-and solid-phase glycosylations. Synthesis of a-linked saccharides and construction of disaccharide libraries using phenylsulfenyl 2-deoxy-2-trifluoroacetamido glycopyranosides as glycosyl donors
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(b) Silva, D. J.; Wang, H.; Allanson, N. M.; Jain, R. K.; Sofia, M. J. Stereospecific solution-and solid-phase glycosylations. Synthesis of a-linked saccharides and construction of disaccharide libraries using phenylsulfenyl 2-deoxy-2-trifluoroacetamido glycopyranosides as glycosyl donors. J. Org. Chem. 1999, 64 (16), 5926-5929.
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84922364919
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N-allyloxycarbonyl derivatives of D-glucosamine as promotors of 1,2-trans-glycosylation in Koenigs-Knorr reactions and in Lewis acid catalyzed condensations
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Boullanger, P.; Banoub, J.; Descotes, G. N-Allyloxycarbonyl derivatives of D-glucosamine as promotors of 1,2-trans-glycosylation in Koenigs-Knorr reactions and in Lewis acid catalyzed condensations. Can. J. Chem. 1987, 65, 1343-1348.
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N, N-diacetylglucosamine and galactosamine derivatives as glycosyl donors
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The 2-N, N-dibenzylamino group as a participating group in the synthesis of b-glycosides
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24
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0001306231
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Vergleichende untersuchungen zur abspaltung substit. Benzylreste vom amidstickstoff und deren kombinationsmöglichkeiten mit urethanschutzgruppen
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(b) Weygand, F.; Steglich, W.; Bjarnason, J.; Akhtar, R.; Chytil, N. Vergleichende Untersuchungen zur Abspaltung Substit. Benzylreste vom Amidstickstoff und deren Kombinationsmöglichkeiten mit Urethanschutzgruppen. Chem. Ber. 1968, 101, 3623-3641.
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0001806588
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Use of protecting groups in carbohydrate chemistry
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27
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49549143786
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Coupure sélective par l’hydrazine des groupements acétyles anomères de résidus glycosyles acétylés
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Neue methoden zur glycosid-und oligosaccharidesynthese - Gibt es alternativen zur Koenigs-Knorr-methode?
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0034695635
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Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring
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We have recently reported that D-glucosamine and derivatives can be anchored to a solid support at the amine/nitrogen through a tris(alkoxy)benzyl BAL handle in a ’safety-catch’ manner. When the anchoring is through the secondary amine, the anchoring is relatively acid-stable. Upon N-acylation to form the acylamine, the anchoring linkage becomes labile to coned TFA: Tolborg J.F.; Jensen, K.J. Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring. Chem. Commun. 2000, 147-148.
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34
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85020981976
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note
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Due to the very thick precipitate formed during the reaction, a mechanical stirrer was initially employed for efficient mixing of the reagents. However, it was found that carrying out the reaction in a beaker and shaking the reagents for 18 h afforded both efficient mixing and facilitation of the work-up procedure.
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