Syntheses of all the possible monomethyl ethers and several deoxyhalo analogues of methyl β-lactoside as ligands for the Ricinus communis lectins

Abstract

The synthesis of all the possible monomethyl ethers of methyl β-lactoside ( 1) has been performed from 1 in a straighforward way, making use of the different reactivity of the hydroxyl groups in alkylation and stannlation reactions. In addition, the deoxyfluoro derivatives of 1 at positions, 6, 3′, 4′, epi-4′, and 6′ have been prepared by reaction of the appropriate substrates with diethylaminosulfur trifluoride or tetrabutylammonium fluoride. Finally, the 6-deoxyiodo and 6′-bromodeoxy analogues of 1 have also been prepared.