SYNTHESIS OF CELLOBIOSE, CELLOTRIOSE, CELLOTETRAOSE, AND LACTOSE

Article abstract of DOI:10.1016/0008-6215(83)84014-2

Condensation of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (1) with benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (6) in 1:1 benzene-nitromethane in the presence of mercuric cyanide gave, in 86percent yield after O-deacetylation followed by column chromatography, benzyl 2,3,6-tri-O-benzyl-β-cellobioside, which was catalytically hydrogenolyzed to afford cellobiose.In a similar way, methyl-α-cellobioside cellotriose, methyl-α- and β-cellotriosides, cellotetraose, lactose, and methyl α-lactoside were synthesized with high stereospecificity and in good yield by the coupling reaction, using methyl 2,3,6-tri-O-benzyl-α- and -β-D-glucopyranosyde, 6, and benzyl 2,3,6,2',3',6'-hexa-O-benzyl-β-cellobioside as the glycosyl acceptors, and 1, 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide, and hepta-O-acetyl-α-cellobiosyl bromide as the glycosyl donors.