Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 35, Pages 13926-13929Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2062715
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Funding
- NSERC
- Merck Research Laboratories (CADP)
- CFI
- Province of Ontario
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A derivative of diphenylborinic add promotes catalytic, regioselective Koenigs-Knorr glycosylations of carbohydrate derivatives bearing multiple secondary hydroxyl groups. Robust levels of selectivity for the equatorial OH group of cis-1,2-diol motifs are demonstrated in reactions of seven acceptors derived from galactose, mannose, fucose, and arabinose using a variety of glycosyl halide donors. Catalyst control presents a new means of generating defined glycosidic linkages from unprotected or minimally protected carbohydrate feedstocks.
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