Myristoyl esters of lactose

Whereas lactose did not undergo a base-catalyzed transesterification with methyl esters of fatty acids, methyl beta-lactoside reacted under identical conditions to give mono- and di-myristates. This difference in behavior is explained in terms of the formation of an unreactive, internally chelated potassium-lactose complex. Supporting evidence for this hypothesis is the observed change in the anomeric equilibrium of lactose in the presence of potassium carbonate. The monomyristates of methyl beta-lactoside were assigned the structures of 3' and 6' derivatives, and it is concluded that the diesters are the 3',6', and 6,6' derivatives.