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|Title:||Dihydroxylation of 4-substituted 1,2-dioxines: A concise route to branched erythro sugars|
|Citation:||Journal of Organic Chemistry, 2009; 74(14):5093-5096|
|Publisher:||Amer Chemical Soc|
|Tony V. Robinson, Daniel Sejer Pedersen, Dennis K. Taylor and Edward R. T. Tiekink|
|Abstract:||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.|
|Keywords:||Erythritol; Dioxins; Carbohydrates; Molecular Structure; Oxidation-Reduction; Hydroxylation; Stereoisomerism|
|Description:||Copyright © 2009 American Chemical Society|
|Appears in Collections:||Chemistry and Physics publications|
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