6533b82ffe1ef96bd1294900
RESEARCH PRODUCT
Selective isomerization of a trans -butanediacetal derivative of tartaric acid with differentiating substituents at C-2 and C-3
Adam DropHubert WojtasekBożena Frąckowiak-wojtaseksubject
chemistry.chemical_classification010405 organic chemistryStereochemistryOrganic Chemistryenolateselective isomerization010402 general chemistryThioester01 natural sciencesBiochemistry0104 chemical scienceschemistry.chemical_compoundFukuyama reductionbutanediacetalschemistryYield (chemistry)Drug DiscoveryTartaric acidFukuyama reductionIsomerizationDerivative (chemistry)description
Abstract 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-04-01 | Tetrahedron Letters |