Myristoyl esters of lactose

Abstract

Whereas lactose did not undergo a base-catalyzed transesterification with methyl esters of fatty acids, methyl β-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 β-lactoside were assigned the structures of 3′ and 6′ derivatives, and it is concluded that the diesters are the 3′,6t́, and 6,6′ derivatives.