The synthesis of new glycoside surfactants by means of halogenated sugars. Thioethers and methyl sulfone derivatives of α-D-glucoside and α-D-mannoside

Article abstract of DOI:10.1016/S0040-4020(01)87130-1

We describe an efficient synthesis of methyl 6-halogeno-6-deoxyglycosides which was performed using Ph₃P-X₂ in DMF solution. Carbohydrate halides could thus be isolated in high yields without preliminary protection of the secondary hydroxyl groups, and were used as intermediates for the preparation of 6-alkylthio- and 6-alkylsulfonyl-6-deoxy glycosides. These derivatives are new non-ionic chiral surfactants.