Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis
| Autor: | Robert Dhal, Pavlo Shpak-Kraievskyi, Biaolin Yin, Mathieu Y. Laurent, Arnaud Martel, Gilles Dujardin |
|---|---|
| Přispěvatelé: | Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2012 |
| Předmět: |
medicine.drug_class
Stereochemistry peptide aldehyde Peptide Carboxamide 010402 general chemistry 01 natural sciences Biochemistry Aldehyde Chemical synthesis Maraviroc chemistry.chemical_compound β-amino acetal Drug Discovery Peptide synthesis medicine Enantiomeric excess Peptide coupling ComputingMilieux_MISCELLANEOUS chemistry.chemical_classification 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Acetal 0104 chemical sciences chemistry Transacetalization Amine gas treating |
| Zdroj: | Tetrahedron Tetrahedron, Elsevier, 2012, 68 (9), pp.2179-2188. ⟨10.1016/j.tet.2012.01.002⟩ |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2012.01.002⟩ |
| Popis: | Efficient access to masked β-amino-aldehydes was performed starting from 6-alcoxy tetrahydrooxazinone 6a–d (6-ATO). Transacetalization leads to the opening of the cycle to form either unsymmetric acetal 7 or symmetric acetals 16–18. These amino acetals are key compounds, obtained with 99% ee, which can be engaged in efficient peptide coupling. This method could easily provide peptides aldehydes or small amido aldehydes as exemplified with the formal synthesis of ent-Maraviroc. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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