ACTION OF BASE ON THE DI-O-METHANESULFONYL ESTERS OF METHYL ALPHA-D-GLUCOPYRANOSIDE - DISPLACEMENT ORDER AND END PRODUCTS

Action of base on the six methyl di-O-methanesulfonyl-a-D-glucopyranosidesgave a series of methyl anhydro-O-methanesulfonyl-a-D-hexosides, which were further transformed by base into either methyl anhydroa-D-hexosides or methyl dianhydro-a-D-hexosides. An order of preference C4 C6 C2 for thevicinal SN2 sulfonyloxy group displacements is discussed. An order of end product preference is suggested among four reactions that methyl anhydro-O-methanesulfonyl-a-D-hexosides commonly undergo with base. This latter preference order accounts for the observed products in the multistepped, second sulfonyloxy group removal. The unreported methyl 2, 4- and 3, 6-di-O-methanesulfonyl-a-D-glucopyranosides (as their di-O-benzoyl products) were prepared for this study. © 1979, American Chemical Society. All rights reserved.