Hilty, Florentine M; Brun, Kathrin A; Heimgartner, Heinz (2004). A New 2H-Azirin-3-amine as a Synthon for α-Methyl Glutamate. Helvetica Chimica Acta, 87(10):2539-2548.
The synthesis of a novel 2,2-disubstituted 2H-azirin-3-amine 10 as a building block for racemic Glu(2Me) is described. This synthon contains an ester group in the side chain. The reaction of 10 with thiobenzoic S-acid and the amino acid Z-Val-OH yielded the racemic monothiodiamide 17 and the dipeptide 18 as a mixture of diastereoisomers, respectively (Scheme 2). From 18, each of the protecting groups was removed selectively (Scheme 3).
The synthesis of a novel 2,2-disubstituted 2H-azirin-3-amine 10 as a building block for racemic Glu(2Me) is described. This synthon contains an ester group in the side chain. The reaction of 10 with thiobenzoic S-acid and the amino acid Z-Val-OH yielded the racemic monothiodiamide 17 and the dipeptide 18 as a mixture of diastereoisomers, respectively (Scheme 2). From 18, each of the protecting groups was removed selectively (Scheme 3).
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry Life Sciences > Drug Discovery Physical Sciences > Physical and Theoretical Chemistry Physical Sciences > Organic Chemistry Physical Sciences > Inorganic Chemistry |
| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
| Language: | English |
| Date: | 2004 |
| Deposited On: | 13 Aug 2013 15:03 |
| Last Modified: | 30 Jul 2020 09:32 |
| Publisher: | Wiley-Blackwell |
| ISSN: | 0018-019X |
| Funders: | Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Stiftung für wissenschaftliche Forschung an der Universität Zürich, Prof. Dr. Hans E. Schmid-Stiftung |
| OA Status: | Green |
| Publisher DOI: | https://doi.org/10.1002/hlca.200490226 |
| Project Information: |
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Hilty, Florentine M