Conversion of lactose into mimics of N-acetyllactosamine

The α-C-Glycoside of N-acetyllactosamine 8 was synthesised from lactose by acetylation, conversion into the allyl α-C-glycoside 4, exchanging the protecting groups for benzyl ethers, selective deprotection at the gluco-C-2 by iodocyclisation-reductive elimination, and conversion of the free hydroxyl group into an acetamido group by oxidation, oximation, stereoselective reduction and acetylation. Isomerization of the C-glycosidic appendage by conversion into a 2-oxypropyl group and treatment with base gave, after acetylation, the β-C-glycoside of N-acetyllactosamine 11.