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 language | English (US) |
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Pages (from-to) | 7561-7564 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 67 |
Issue number | 21 |
DOIs | |
State | Published - Oct 18 2002 |
Externally published | Yes |