Publication

Enzymatic desymmetrization of 1,1 '-methylenedi-[(1R,1 ' S,3R,3 ' S,5S,5 ' R)-3-hydroxy-8-oxabicyclo[3.2.1]-oct-6-ene-1-yl]: Novel precursors of long chain polyketides

Sandrine Gerber, Gérald Coste
2005
Journal Articles

Abstract

meso-1,1'-Methylenedi[(1R,1'S,3R,3'S,5S,5'R)-3-hydroxy-S-oxabicyclo[3.2. 1]oct-6-ene-1-yl] 14 obtained through the [4+3]-cycloaddition of 2,T-methylenedifuran to oxyallyl cation, followed by reduction, has been desymmetrized by means of a lipase catalyzed transesterification to afford (1 S,3S,5S)-1-[(1 R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2. 1]oct-6-en-yl]methyl)-8-oxabicyclo[3.2.1]loct-6-en-3-yl acetate (-)-15 (89% ee). This compound was transformed into aromatic ester derivatives for establishing the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.

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https://infoscience.epfl.ch/entities/publication/4c3ddb58-030b-4112-b2a8-bcb510eedaa7

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Sandrine Gerber, Gérald Coste
2005
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/4c3ddb58-030b-4112-b2a8-bcb510eedaa7

About this result

Related concepts (7)

Ester

In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (). Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC.

Phosphite ester

In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. They can be considered as esters of an unobserved tautomer phosphorous acid, H3PO3, with the simplest example being trimethylphosphite, P(OCH3)3. Some phosphites can be considered esters of the dominant tautomer of phosphorous acid (HP(O)(OH)2). The simplest representative is dimethylphosphite with the formula HP(O)(OCH3)2. Both classes of phosphites are usually colorless liquids.

Peptide

Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides which have a molecular mass of 10,000 Da or more are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides. Peptides fall under the broad chemical classes of biological polymers and oligomers, alongside nucleic acids, oligosaccharides, polysaccharides, and others.

Related publications (12)

Enzymatic desymmetrization of 1,1 '-methylenedi-[(1R,1 ' S,3R,3 ' S,5S,5 ' R)-3-hydroxy-8-oxabicyclo[3.2.1]-oct-6-ene-1-yl]: Novel precursors of long chain polyketides

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