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.

Graphical abstractFour 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 full-size imageDownload as PowerPoint slide