SYNTHESIS OF FLUORINE-CONTAINING NATURAL GASTRODIN AND ITS ANALOGUES

Article abstract of DOI:10.1016/S0022-1139(00)82922-X

Reactions of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (2) with p-hydroxybenzaldehyde, trifluoromethyl and fluoro substituted aniline and 2-amino-6-fluorobenzoic acid gave 1-O-(p-formylphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (3), 1-N-(m-trifluoromethylphenylamino)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4a), 1-N-(2-carboxyl-3-fluorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4b) and 1-N-(p-fluorophenyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4c) respectively. 1-O-(perfluoro-2-propoxypropionyl)-O-benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7) and 1-O-(m-trifluoromethylphenylaminobenzylidene)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (8) were also prepared in subsequent reactions.Conversion of the acetyl group to the hydroxyl group yielded the corresponding deprotected product.The compounds formed have been characterized by analysis, IR, 1H and 19F NMR and mass spectroscopy.The influence of phase-transfer catalysts on the reactions is discussed.