Solid-Phase Transimidation for the Removal of N-Phthalimido- and N-Tetrachlorophthalimido Protecting Groups on Carbohydrates

Peter Stangier; Ole Hindsgaul

doi:10.1055/s-1996-5356

Synlett 1996; 1996(2): 179-181
DOI: 10.1055/s-1996-5356

letter

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Solid-Phase Transimidation for the Removal of N-Phthalimido- and N-Tetrachlorophthalimido Protecting Groups on Carbohydrates

Peter Stangier, Ole Hindsgaul^*

^*Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada, Fax (403)-492-7705; Bitnet Ole.Hindsgaul@Ualberta.Ca

Abstract

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N-Phthalimido and N-tetrachlorophthalimido groups on carbohydrate derivatives are conveniently deprotected using alkyldiamines immobilized on polystyrene beads. The protecting group and reagent remain on the beads and the free amino sugar is recovered in 81-96% yield by simple filtration and evaporation.

Phthalimido - tetrachlorophthalimido deprotection - immobilized amines

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