Journal article
Synthesis of a carbon analogue of N-acetylmannosamine via acetolysis on a relatively stable ozonide
Journal of organic chemistry, Vol.67(21), pp.7561-7564
10/18/2002
DOI: 10.1021/jo020362k
PMID: 12375999
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 alpha-acetate.
Details
- Title: Subtitle
- Synthesis of a carbon analogue of N-acetylmannosamine via acetolysis on a relatively stable ozonide
- Creators
- Liqiang Chen - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USADavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.67(21), pp.7561-7564
- DOI
- 10.1021/jo020362k
- PMID
- 12375999
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Grant note
- DK 54759 / NIDDK NIH HHS
- Language
- English
- Date published
- 10/18/2002
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9983985956302771
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