Short efficient syntheses of epimeric C6-C-methyl glucoses are described. One C-6 epimer activates glycogen synthase while the other epimer inactivates the enzyme; C6R-C-methyl glucose 3 is the first example of a specific inhibitor of glucose-6-phosphatase and can increase the intracellular concentration of glucose-6-phosphate 20 times. C6S-C-methyl glucose 2 inhibits glucokinase and glucose-6-phosphatase, but also has the potential to give easy access to α-C-glycosides of L-fucose, C-6-Alkyl carbohydrates may provide a new range of sugar mimics that control enzymes associated with formation, hydrolysis and other fates of sugar-6-phosphates.
