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
| العنوان: | 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 |
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| المؤلفون: | Hermann Petersen, Alfred Popp, Andrea Gilch, Anne-Laure Mersier, Jodoca Rockinger-Mechlem, Jürgen Dr. Dipl.-Chem. Stohrer |
| المصدر: | Advanced Synthesis & Catalysis. 346:682-690 |
| بيانات النشر: | Wiley, 2004. |
| سنة النشر: | 2004 |
| مصطلحات موضوعية: | biology, Chemistry, Stereochemistry, General Chemistry, biology.organism_classification, Kinetic resolution, Nucleoside Reverse Transcriptase Inhibitor, chemistry.chemical_compound, Enantiopure drug, Nucleophile, biology.protein, Amdoxovir, Candida antarctica, Solvolysis, Lipase |
| الوصف: | The resolution of racemic 1,3-dioxolan-4-one and 1,3-oxathiolan-5-one derivatives such as (4-oxo-1,3-dioxolan-2-yl)methyl 2-methylpropanoate (2) by enzymatic solvolysis was investigated. The resolution of 2, a precursor for the synthesis of the nucleoside reverse transcriptase inhibitor Amdoxovir, was optimized in terms of solvent/nucleophile, reaction conditions, and enzyme. The use of lipase from Candida antarctica B (CALB) and methanol as nucleophile and solvent resulted in an effective resolution and the product (R)-2 could be easily isolated. Products of substrate decomposition can be isolated and reused for the synthesis of racemic 2. The broad range of application for this enzymatic resolution was demonstrated by the resolution of further substrates with different substitution patterns. This process gives a new and unprecedented access to enantiopure 1,3-dioxolan-4-ones and 1,3-oxathiolan-5-ones. |
| تدمد: | 1615-4169 1615-4150 |
| DOI: | 10.1002/adsc.200303184 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::f79625c17c67951e3840eecd24bef4b4 https://doi.org/10.1002/adsc.200303184 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi...........f79625c17c67951e3840eecd24bef4b4 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 16154169 16154150 |
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| DOI: | 10.1002/adsc.200303184 |