Monosaccharides as internal probes for the determination of the absolute configuration of 2-butanol

✍ Scribed by Patrycja Seroka; Marcin Płosiński; Jacek Czub; Paweł Sowiński; Jan Pawlak

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 186 KB
• Volume: 44
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1735

✦ Synopsis

D-Glucose, D-mannose and L-rhamnose were reacted with a racemic mixture of 2-butanol, and the resulting alpha-glycosides were analyzed by 1H NMR with COSY and NOESY experiments. Conformational analysis of alpha-glycosidic bonds performed with molecular modeling and appropriate heteronuclear long-range coupling measurements and combined with analysis of dipolar couplings observed in NOESY spectra allowed the assignment of absolute configuration in the aglycones of elucidated alpha-glycosides.