Glucosamine derived DISAL donors for stereoselective glycosylations under neutral conditions

S. Grathe, M.B. Thygesen, K. Larsen, L. Petersen, Knud Jørgen Jensen

Research output: Contribution to journalJournal articleResearchpeer-review


DISAL (methyl 3,5-dinitrosa/icylate) D-glcosyl, D-galactosyl, D-mannosyl, and L-quinovosyl donors have previously provided the efficient glycosylation of a range of substrates under either strictly neutral, mildly basic, or very mildly Lewis acidic (LiClO4) conditions. Herein we report the synthesis of new glucosamine DISAL donors, carrying N-TCP, -Troc, or -TFAc protecting groups, and their use in beta-(1,2-trans) selective glycosylations, primarily in NMP in the absence of any added Lewis acids, or in CH3NO2 with LiClO4. Finally, precise microwave heating proved effective in promoting the difficult glycosylation of the 3-OH of a glucosamine derivative.
Original languageEnglish
Issue number8
Pages (from-to)1439-1448
Publication statusPublished - 2005


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