Regioselective synthesis of 6-S-alkyl and 6-S-glycosyl-6-thio-D-mannofuranose derivatives from 5,6-O-cyclic sulfate precursors.
C-6 opening of 5,6-cyclic sulfate derivatives of mannofuranose with a thiolate anion followed by acidic hydrolysis of the acyclic sulfate gave 6-S-alkyl derivatives in good yields (70-95%) and short reaction times (10-15min). This methodology was applied to the synthesis of methyl 2,3-O-isopropylidene-6-S-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)-6-thio-alpha-d-mannofuranoside (70%), 2,3-O-isopropylidene-6-S-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)-6-thio-alpha-d-mannofuranose (87%) and 2,3-O-isopropylidene-6-S-(1,2:3,4-di-O-isopropylidene-alpha-d-galactopyranos-6-yl)-6-thio-alpha-d-mannofuranose (87%).
Wadouachi
Anne
A
Laboratoire des Glucides UMR 6219, Université de Picardie Jules Verne, 33 Rue Saint-Leu, F-80039 Amiens, France. anne.wadouachi@u-picardie.fr
Lescureux
Ludivine
L
Lesur
David
D
Beaupère
Daniel
D
D003499:Cyclic S-Oxides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008362:Mannosides / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis*; D013431:Sulfates / Q000737:chemistry
C453001:2,3-O-isopropylidene-mannofuranose; D003499:Cyclic S-Oxides; D008362:Mannosides; D009005:Monosaccharides; D013431:Sulfates; D008358:Mannose