SYNTHESES OF ALL THE POSSIBLE MONOMETHYL ETHERS AND SEVERAL DEOXYHALOANALOGS OF METHYL BETA-LACTOSIDE AS LIGANDS FOR THE RICINUS-COMMUNIS LECTINS

The synthesis of all the possible monomethyl ethers of methyl beta-lac toside (1) has been performed from 1 in a straightforward way, making use of the different reactivity of the hydroxyl groups in alkylation a nd stannylation reactions. In addition, the deoxyfluoro derivatives of 1 at positions, 6, 3', 4', epi-4', and 6' have been prepared by react ion of the appropriate substrates with diethylaminosulfur trifluoride or tetrabutylammonium fluoride. Finally, the 6-deoxyiodo and 6'-bromod eoxy analogues of 1 have also been prepared.