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

Abstract
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.

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