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Trimethylene Dithioacetals of Carbohydrates, Part 6: C-C Coupling Reactions of Dilithiated N-Acetyl-D-glucosamine Trimethylene Dithioacetal Derivatives

Yue-Lei Chen, Robin Leguijt, Hartmut Redlich*, Roland Fröhlich

*Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany, Email:

Y.-L. Chen, R. Leguijt, H. Redlich, R. Fröhlich, Synthesis, 2006, 4212-4218.

DOI: 10.1055/s-2006-950359


While 3,4;5,6-di-O-isopropylidene-N-phthaloyl-D-glucosamine propane-1,3-diyl dithioacetal underwent fast β-elimination, the corresponding N-acetyl derivative was easily deprotonated with butyllithium to form the dilithiated intermediate. Stoichiometry and temperature were crucial factors for selective C-C coupling with various electrophiles.

see article for more examples

formation of the 1,2-elimination product using phthalimide

Key Words

D-glucosamine trimethylene dithioacetal, chiral pool, carbanion, imidate anion, chain extension, α-keto esters, α-hydroxy ketones, 1,3-dithianes, Corey-Seebach reaction, phthalimides

ID: J66-Y2006-4240