Synthesis of Potassium (2R)-2-O-alpha-D-Mannopyranosyl-(1 -> 2)-alpha-D-glucopyranosyl-2,3-dihydroxypropanoate: A Naturally Compatible Solute

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An expedient synthesis of the potassium salt of (2R)-2-O-alpha-D-mannopyranosyl-(1 -> 2)-alpha-D-glucopyranosyl-2,3-dihydroxypropanoic acid (MGG)-a recently isolated, rare, compatible solute-was accomplished. A bis-acetal-protected thioglucoside, 6-OTBDPS, with a 2-OH group was used as the acceptor in the first glycosylation reaction with tetraacetylman-nosyl trichloroacetimidate, and as the donor in the glycosylation reaction with the glycerate derivative. The a anomer was the only product of both glycosylation reactions, as expected for the formation of the a-mannoside. The formation of the 1,2-cis glucoside was more challenging.
Original languageUnknown
Pages (from-to)6698-6703
JournalEuropean Journal of Organic Chemistry
Issue number33
Publication statusPublished - 1 Jan 2011

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