Synthesis of a carbon analogue of N-acetylmannosamine via acetolysis on a relatively stable ozonide

Liqiang Chen, David F. Wiemer

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

After a 2-methylpropenyl group was added to a carbohydrate framework through regioselective opening of a glucose-derived epoxide, hydrolysis or acetolysis of the methyl glycoside in various derivatives was problematic. Ozonolysis of the olefin followed by brief treatment with dimethyl sulfide gave a mixture of diastereomeric ozonides that proved to be stable for weeks at room temperature. Acetolysis of these ozonides at low temperature allowed selective cleavage of the methyl glycoside in the presence of the 1,2,4-trioxolane as well as selective formation of the α-acetate.

Original languageEnglish (US)
Pages (from-to)7561-7564
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number21
DOIs
StatePublished - Oct 18 2002
Externally publishedYes

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