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

Authors
Jimenez-Barbero, J Demange, R Schenk, K Vogel, P
Citation
J. Jimenez-barbero et al., 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, J ORG CHEM, 66(15), 2001, pp. 5132-5138
Citations number
74
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
15
Year of publication
2001
Pages
5132 - 5138
Database
ISI
SICI code
0022-3263(20010727)66:15<5132:SASCAO>2.0.ZU;2-#
Abstract
Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde w ith isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside th at was converted into the title C-disaccharide 1. Its conformational behavi or in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.