Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid

The Journal of Organic Chemistry
Oskar PopikDavid Crich

Abstract

The synthesis of a legionaminic acid donor from N-acetylneuraminic acid in 15 steps and 17% overall yield is described. Activation of the adamantanyl thioglycoside in the donor with N-iodosuccinimide and trifluoromethanesulfonic acid in dichloromethane and acetonitrile at -78 °C in the presence of primary, secondary and tertiary alcohols affords the corresponding glycosides in excellent yield and good to excellent equatorial selectivity. In particular, coupling to the 4-OH of a suitably protected neuraminic acid derivative affords a disaccharide that closely resembles the glycosidic linkage in the polylegionaminic acid from the lipopolysaccharide of the Legionella pneumophila virulence factor. A straightforward deprotection sequence enables conversion of the protected glycosides to the free N,N-diacetyllegionaminic acid glycosides.

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Jan 6, 2016·Journal of the American Chemical Society·Szymon Buda, David Crich
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Citations

Feb 10, 2021·Carbohydrate Research·Parasuraman RajasekaranDavid Crich
Jun 26, 2018·Chemical Reviews·Chryssostomos ChatgilialogluVitaliy I Timokhin
Aug 25, 2017·Journal of the American Chemical Society·Han LiuXuechen Li

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