The synthesis of 2-, 3-, 4- and 6-O-α-d-glucopyranosyl-d-galactopyranose, and their evaluation as nutritional supplements for pre-term infants

Four methods have been screened for the synthesis of some α-d-glucopyranosides, with the recently reported (Mukaiyama) combination of 2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl iodide and triphenylphosphine oxide being the most successful, especially in the diastereoselectivity exhibited. The α-d-glucopyranosides so obtained have been deprotected to yield 2-, 3-, 4- and 6-O-α-d-glucopyranosyl-d-galactopyranose. Only the last disaccharide showed any hydrolysis by α-glycosidases but this success was not emulated by mucosal extracts from the small intestine of the pig.

Four methods have been screened for the synthesis of various structural isomers of O-α-d-glucopyranosyl-d-galactopyranose. One of these isomers, namely 6-O-α-d-glucopyranosyl-d-galactopyranose, showed some potential as a nutritional supplement for pre-term infants.Figure optionsDownload as PowerPoint slide