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.
2001
66
15
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5138
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.
REVIEWED
EPFL