Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry.
S-Glycosyl thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named "glycosyl Bunte salts" after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water-acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation reactions into other glycosyl compounds such as a 1-thio sugar, a glycosyl disulfide, a 1,6-anhydro sugar, and an O-glycoside.
Meet the Board of ChemistryOpen: Antony J. Fairbanks
Abstract Antony J. Fairbanks is a Professor in the Department of Chemistry at the University of Canterbury in New Zealand. The research of his group focuses on the broad areas of organic synthesis, particularly applied to carbohydrates. He currently serves as an active Editorial Board member for ChemistryOpen.
Synthesis of O-α-D-galactopyranosyl-(1 → 2)-O-α-D-glucopyranosyl-(1 → 1)-D-glycerol, a degradation product of the glycolipid from a pneumococcus
O-α-D-Galactopyranosyl-(1 → 2)-O-α-D-glucopyranosyl-(1 → 1)-D-glycerol has been synthesised by a Koenigs–Knorr reaction from 2-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide and methylenebis-2-O-(3-O-benzyl-D-glycerol) followed by removal of protecting groups. The reaction using the corresponding β-chloride also yielded the desired product but in lower overall yield. The synthetic glycoside was identical with the galactosylglucosyglycerol isolated by degradation of the major glycolipid from a rough strain of Pneumococcus, Type I.