Selective isomerization of a trans -butanediacetal derivative of tartaric acid with differentiating substituents at C-2 and C-3
| Autor: | Adam Drop, Hubert Wojtasek, Bożena Frąckowiak-Wojtasek |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Stereochemistry Organic Chemistry enolate selective isomerization 010402 general chemistry Thioester 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound Fukuyama reduction butanediacetals chemistry Yield (chemistry) Drug Discovery Tartaric acid Isomerization Derivative (chemistry) |
| Zdroj: | Tetrahedron Letters. 58:1453-1455 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2017.02.072 |
| Popis: | A trans-disubstituted butanediacetal derivative with two different substituents (ester and thioester) – methyl (2R,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate, was selectively converted to the cis derivative – methyl (2S,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxylate in high yield on a multigram scale. The product of this reaction offers the possibility for selective modification of one of the substituents, which was demonstrated by Fukuyama reduction of the thioester group. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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