Bifunctional Azido(thio)ureas from an <i>O</i>-Protected 2-Amino-2-deoxy-<span style="font-variant: small-caps">d</span>-glucopyranose: Synthesis and Structural Analyses
This publication reports a facile and convenient preparation of tri-<i>O</i>-acetyl-glucopyranoses, derived from the corresponding 2-deoxyaminosugar, where the vicinal anomeric and C2 positions are decorated by azido and (thio)ureido groups, respectively. This double functionalization le...
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MDPI AG
2024-11-01
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| Online Access: | https://www.mdpi.com/1420-3049/29/23/5687 |
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| author | Concepción Sosa-Gil Esther Matamoros Pedro Cintas Juan C. Palacios |
| author_facet | Concepción Sosa-Gil Esther Matamoros Pedro Cintas Juan C. Palacios |
| author_sort | Concepción Sosa-Gil |
| collection | DOAJ |
| description | This publication reports a facile and convenient preparation of tri-<i>O</i>-acetyl-glucopyranoses, derived from the corresponding 2-deoxyaminosugar, where the vicinal anomeric and C2 positions are decorated by azido and (thio)ureido groups, respectively. This double functionalization leads to an inherently chiral core incorporating the versatile azido and (thio)ureido linkages prone to further manipulation. The latter also provides a structural element for hydrogen-bonded donor-acceptor (HB-DA) sites, which are of immense value in organocatalytic pursuits. A computation-aided conformational analysis unveils the landscape of available conformers and their relative stability. <i>N</i>-aryl (thio)ureas bearing substituents at ortho positions exist as mixtures of <i>M</i>- and <i>P</i>-atropisomeric conformers. |
| format | Article |
| id | doaj-art-180fca6c71dc453c9efb8b7c35856aee |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-180fca6c71dc453c9efb8b7c35856aee2024-12-13T16:28:42ZengMDPI AGMolecules1420-30492024-11-012923568710.3390/molecules29235687Bifunctional Azido(thio)ureas from an <i>O</i>-Protected 2-Amino-2-deoxy-<span style="font-variant: small-caps">d</span>-glucopyranose: Synthesis and Structural AnalysesConcepción Sosa-Gil0Esther Matamoros1Pedro Cintas2Juan C. Palacios3Departamento de Química Orgánica e Inorgánica, Facultad de Ciencias, and Instituto del Agua, Cambio Climático y Sostenibilidad (IACYS)-Unidad de Química Verde y Desarrollo Sostenible, Universidad de Extremadura, 06006 Badajoz, SpainDepartamento de Química Orgánica e Inorgánica, Facultad de Ciencias, and Instituto del Agua, Cambio Climático y Sostenibilidad (IACYS)-Unidad de Química Verde y Desarrollo Sostenible, Universidad de Extremadura, 06006 Badajoz, SpainDepartamento de Química Orgánica e Inorgánica, Facultad de Ciencias, and Instituto del Agua, Cambio Climático y Sostenibilidad (IACYS)-Unidad de Química Verde y Desarrollo Sostenible, Universidad de Extremadura, 06006 Badajoz, SpainDepartamento de Química Orgánica e Inorgánica, Facultad de Ciencias, and Instituto del Agua, Cambio Climático y Sostenibilidad (IACYS)-Unidad de Química Verde y Desarrollo Sostenible, Universidad de Extremadura, 06006 Badajoz, SpainThis publication reports a facile and convenient preparation of tri-<i>O</i>-acetyl-glucopyranoses, derived from the corresponding 2-deoxyaminosugar, where the vicinal anomeric and C2 positions are decorated by azido and (thio)ureido groups, respectively. This double functionalization leads to an inherently chiral core incorporating the versatile azido and (thio)ureido linkages prone to further manipulation. The latter also provides a structural element for hydrogen-bonded donor-acceptor (HB-DA) sites, which are of immense value in organocatalytic pursuits. A computation-aided conformational analysis unveils the landscape of available conformers and their relative stability. <i>N</i>-aryl (thio)ureas bearing substituents at ortho positions exist as mixtures of <i>M</i>- and <i>P</i>-atropisomeric conformers.https://www.mdpi.com/1420-3049/29/23/5687azido(thio)ureasamino sugarsatropisomersconformational analysiscarbohydrate synthesiscomputational chemistry |
| spellingShingle | Concepción Sosa-Gil Esther Matamoros Pedro Cintas Juan C. Palacios Bifunctional Azido(thio)ureas from an <i>O</i>-Protected 2-Amino-2-deoxy-<span style="font-variant: small-caps">d</span>-glucopyranose: Synthesis and Structural Analyses Molecules azido(thio)ureas amino sugars atropisomers conformational analysis carbohydrate synthesis computational chemistry |
| title | Bifunctional Azido(thio)ureas from an <i>O</i>-Protected 2-Amino-2-deoxy-<span style="font-variant: small-caps">d</span>-glucopyranose: Synthesis and Structural Analyses |
| title_full | Bifunctional Azido(thio)ureas from an <i>O</i>-Protected 2-Amino-2-deoxy-<span style="font-variant: small-caps">d</span>-glucopyranose: Synthesis and Structural Analyses |
| title_fullStr | Bifunctional Azido(thio)ureas from an <i>O</i>-Protected 2-Amino-2-deoxy-<span style="font-variant: small-caps">d</span>-glucopyranose: Synthesis and Structural Analyses |
| title_full_unstemmed | Bifunctional Azido(thio)ureas from an <i>O</i>-Protected 2-Amino-2-deoxy-<span style="font-variant: small-caps">d</span>-glucopyranose: Synthesis and Structural Analyses |
| title_short | Bifunctional Azido(thio)ureas from an <i>O</i>-Protected 2-Amino-2-deoxy-<span style="font-variant: small-caps">d</span>-glucopyranose: Synthesis and Structural Analyses |
| title_sort | bifunctional azido thio ureas from an i o i protected 2 amino 2 deoxy span style font variant small caps d span glucopyranose synthesis and structural analyses |
| topic | azido(thio)ureas amino sugars atropisomers conformational analysis carbohydrate synthesis computational chemistry |
| url | https://www.mdpi.com/1420-3049/29/23/5687 |
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