Ruthenium-Catalyzed Regioselective Olefin Migration of Dihydropyran Acetals: A De Novo Strategy toward β-2,6-Dideoxypyranoglycosides
| Autor: | Kyeongdeok Seo, Young Ho Rhee |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement Olefin fiber 010405 organic chemistry Dihydropyran Organic Chemistry Regioselectivity chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis Ruthenium chemistry.chemical_compound chemistry Trisaccharide Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 22:2178-2181 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.0c00279 |
| Popis: | Here, we report a de novo synthetic strategy toward β-2,6-dideoxypyranoglycosides. The key event is the ruthenium-catalyzed regioselective olefin migration of dihydropyran allylic acetals to homoallylic acetals. In combination with other metal-catalyzed reactions, this new protocol led to the synthesis of β-2,6-dideoxypyranoglycosides in a highly efficient manner. Using this sequential metal catalysis, various mono-, di-, and trisaccharide forms of β-2,6-dideoxypyranoglycosides were prepared. |
| Databáze: | OpenAIRE |
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