Dihydroxylation of 4-Substituted 1,2-Dioxines: A Concise Route to Branched Erythro Sugars
| Autor: | Daniel Sejer Pedersen, Tony V. Robinson, D. K. Taylor, Edward R. T. Tiekink |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Molecular Structure
Stereochemistry Organic Chemistry Carbohydrates Enantioselective synthesis Diastereomer Stereoisomerism Erythritol Dioxins Hydroxylation Cleavage (embryo) Chemical synthesis chemistry.chemical_compound chemistry Dihydroxylation Chemical reduction Organic chemistry Sugar Oxidation-Reduction |
| Zdroj: | The Journal of Organic Chemistry. 74:5093-5096 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo900669u |
| Popis: | The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage. |
| Databáze: | OpenAIRE |
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