Enzymatic kinetic resolution of 1,3-dioxolan-4-one and 1,3-oxathiolan-5-one derivatives: Synthesis of the key intermediate in the industrial synthesis of the nucleoside reverse transcriptase inhibitor Amdoxovir

Advanced Synthesis and Catalysis

Volumn 346, Issue 6, 2004, Pages 682-690

  Popp, Alfred ^a   Gilch, Andrea ^a   Mersier, Anne Laure ^a   Petersen, Hermann ^b   Rockinger Mechlem, Jodoca ^a   Stohrer, Jürgen ^a  

^a Consortium F Elektrochemische I ^*  (Germany)

^b WACKER CHEMIE AG   (Germany)

Author keywords

Enzyme catalysis; Kinetic resolution; Lipases; Solvolysis

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 1,3 OXATHIOLANE DERIVATIVE; AMDOXOVIR; METHANOL; RNA DIRECTED DNA POLYMERASE INHIBITOR; SOLVENT; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA ANTARCTICA; DRUG SYNTHESIS; SOLVOLYSIS;

EID: 3042751509     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303184     Document Type: Article

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27. For the calculation of the enantiomeric ratio E of a kinetic resolution it is essential to know either the enantiomeric excess (ee) of the substrate and the product or the extent of conversion c together with one enantiomeric excess (substrate or product). In our case, the resolution of (R,S)-2 affords only one chiral "product", the remaining enantiomer. The actual reaction product of the resolution is the aldehyde 6, which is not chiral. Therefore for the calculation of the E value an appropriate method for the determination of the conversion rate was necessary. On an industrial scale the measurement of c with NMR spectroscopic methods is sufficient and, what is more important, easy and fast. On a laboratory scale we used another method. The conversion c was determined using an internal standard. This method provided reliable and precise data. But due to the fact, that even a small variation of the input values (ee or c) causes a significant change in the numerical value E, all stated values were verified by plotting the ee-c diagrams for several extents of conversion so that a best-fit graph could be generated.
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31. The absolute configuration was derived from the known chirality of (R)-2 under the assumption that the stereo-specificity of the lipase does not change under otherwise identical reaction conditions.