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

P.J. Meloncelli, Tracey Williams, Peter Hartmann, Robert Stick

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)1793-1804
JournalCarbohydrate Research
Volume342
DOIs
Publication statusPublished - 2007

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