Protecting Group and Solvent Control of Stereo- and Chemoselectivity in Glucal 3-Carbamate Amidoglycosylation
| Autor: | Sarah E. Bernard, John Decatur, Kimberly M. Sogi, Christian M. Rojas, Ritu Gupta |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Glycosylation
Anomer Biochemistry Article Catalysis chemistry.chemical_compound Combinatorial Chemistry Techniques Organic chemistry Physical and Theoretical Chemistry Chemoselectivity Protecting group Glucal Oxazolidinones chemistry.chemical_classification Molecular Structure Chemistry Alkene Organic Chemistry Hexosamines Stereoisomerism Calcium Gluconate Solvent Stereoselectivity Carbamates Selectivity Mannose |
| Zdroj: | Organic Letters. 11:1527-1530 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol900126q |
| Popis: | In the Rh(2)(OAc)(4)-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 4O and 6O protecting groups. Acyclic protection permits high alpha-anomer selectivity with further improvement in less polar solvents, while electron-withdrawing protecting groups limit C3-oxidized byproducts. Stereocontrol and bifurcation between alkene insertion and C3-H oxidation reflect an interplay of conformational, stereoelectronic, and inductive factors. |
| Databáze: | OpenAIRE |
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