caa a22 4500 467919828 CHVBK 20180406152913.0 cr unu---uuuuu 170328e20060301xx s 000 0 eng 10.1007/s00706-005-0429-1 doi (NATIONALLICENCE)springer-10.1007/s00706-005-0429-1 High-Yield Syntheses of Tetra- O -benzyl-α- D -glucopyranosyl bromide and Tetra- O -pivaloyl-α- D -glucopyranosyl bromide and their Advantage in the Koenigs-Knorr Reaction [Elektronische Daten] [Armin Presser, Olaf Kunert, Irmgard Pötschger] Summary.: Several improved approaches for the preparation of tetra-O-benzyl-α-D-glucopyranosyl bromide and tetra-O-pivaloyl-α-D-glucopyranosyl bromide are discussed. The importance of these compounds, which are useful glycosyl donors, was demonstrated by successful preparation of cholesteryl glucopyranosides in an almost neutral medium without the formation of orthoesters. In addition, accurate 1H and 13C NMR resonance assignments of the synthesized cholesteryl glycosides were performed by 2D NMR spectroscopy. Springer-Verlag/Wien, 2006 Keywords. Koenigs - Knorr reaction nationallicence Glycosidation nationallicence Orthoester nationallicence Cholesteryl glycosides nationallicence Presser Armin Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Karl-Franzens-University of Graz, 8010, Graz, Austria aut Kunert Olaf Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Karl-Franzens-University of Graz, 8010, Graz, Austria aut Pötschger Irmgard Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Karl-Franzens-University of Graz, 8010, Graz, Austria aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/3(2006-03-01), 365-374 0026-9247 137:3<365 2006 137 706 https://doi.org/10.1007/s00706-005-0429-1 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-005-0429-1 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Presser Armin Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Karl-Franzens-University of Graz, 8010, Graz, Austria aut NATIONALLICENCE 700 1- Kunert Olaf Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Karl-Franzens-University of Graz, 8010, Graz, Austria aut NATIONALLICENCE 700 1- Pötschger Irmgard Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Karl-Franzens-University of Graz, 8010, Graz, Austria aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/3(2006-03-01), 365-374 0026-9247 137:3<365 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer