REACTION OF CARBOHYDRATES WITH METHYLSULFONYL CHLORIDE IN N,N-DIMETHYLFORMAMIDE . PREPARATION OF SOME METHYL 6-CHLORO-6-DEOXYGLYCOSIDES

Reaction of hexopyranosides with methylsulfonyl chloride in N,N-dimethylformamide causes selective replacement of the primary hydroxyl groups by chlorine. The resulting 6-chloro-6-deoxyhexopyranosides are reduced to 6-deoxyhexopyranosides by lithium aluminum hydride in tetrahydrofuran. These reactions provide an improvement over current syntheses of 6-chloro-6-deoxyhexopyranosides and 6-deoxyhexopyranosides in the yield and number of steps involved. © 1968, American Chemical Society. All rights reserved.