SYNTHESIS OF DEOXY SUGAR ESTERS: A CHEMOENZYMATIC STEREOSELECTIVE APPROACH AFFORDING DEOXY SUGAR DERIVATIVES ALSO IN THE FORM OF ALDEHYDE
| Autor: | Ly Villo, Luciano Saso, Andrus Metsala, Omar Parve, Tõnis Pehk, Kady Danilas, Imre Vallikivi, Malle Kreen, Sirje Vija |
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| Jazyk: | angličtina |
| Rok vydání: | 2007 |
| Předmět: |
chemistry.chemical_classification
Aldehydes Magnetic Resonance Spectroscopy Stereochemistry Carboxylic acid Organic Chemistry Esters Alkylation Mandelic acid Aldehyde Chemical synthesis Mass Spectrometry chemistry.chemical_compound chemistry Deoxy Sugars Hemiacetal Organic chemistry Deoxy sugar Enantiomeric excess |
| Popis: | A chemoenzymatic synthesis of deoxy sugar esters is described. The synthesis is based on the O-alkylation of carboxylic acid with 2-bromo-5-acetoxypentanal. The method allows treatment of hydroxy carboxylic acids without protection of alcoholic hydroxyl groups. Several stereoisomeric deoxy sugar esters were resolved (up to ee or de > 98%) using a lipase-catalyzed acetylation of hemiacetals that in certain cases afforded deoxy sugar derivatives in the form of aldehydes. The stereochemistry of the reactions was determined by the NMR spectra of mandelic acid derivatives. |
| Databáze: | OpenAIRE |
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