Synthesis and solution conformational analysis of 2,3-anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-hept itol-1-C-yl]-beta-D-gulo-furanose: First example of a monofluoromethylene-linked C-disaccharide
Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.
Keywords: Proton coupling-constants ; mechanics force-fields ; protein-bound state ; c-13 nmr-spectra ; molecular mechanics ; preferred conformation ; lactose ; analog ; o-glycosides ; oligosaccharides ; behavior
Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland. CSIC, Inst Quim Organ, E-28006 Madrid, Spain. Univ Lausanne, Inst Cristallog, BSP, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08