Four methods have been screened for the synthesis of some alpha-D-glucopyrano sides, with the recently reported (Mukaiyama) combination of 2,3,4,6-tetra-O-benzyl- alpha-D-glucopyranosyl iodide and triphenylphosphine oxide being the most successful, especially in the diastereoselectivity exhibited. The alpha-D-glueopyranosides so obtained have been deprotected to yield 2-, 3-, 4- and 6-O-alpha-D-glucopyranosyl-D-galactopyranose. Only the last disaccharide showed any hydrolysis by alpha-glycosidases but this success was not emulated by mucosal extracts from the small intestine of the pig. (c) 2007 Elsevier Ltd. All rights reserved.
Meloncelli, P. J., Williams, T., Hartmann, P., & Stick, R. (2007). The synthesis of 2-, 3-, 4- and 6-O-α-D-glucopyranosyl-D-galactopyranose, and their evaluation as nutritional supplements for pre-term infants. Carbohydrate Research, 342, 1793-1804. https://doi.org/10.1016/j.carres.2007.04.022