Synthesis and solution conformational analysis of 2,3-anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-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-glucopyranosylcarbaldehyde with isolevoglucosenone induced by Et(2)AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoromethylene 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.
Jiménez-Barbero
J
J
Section de Chimie, Université de Lausanne, BCH, CH-1015 Lausanne-Dorigny, Switzerland.
Demange
R
R
Schenk
K
K
Vogel
P
P
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D018360:Crystallography, X-Ray; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data
C433388:2,3-anhydro-3-C-(2,6-anhydro-1-deoxy-1-fluoro-glycero-gulo-heptitol-1-C-yl)-gulo-furanose; D004187:Disaccharides