(1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate
Treatment of <i>N</i>-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single crystal X-ray diffraction analysi...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-02-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2022/1/M1337 |
| _version_ | 1797444500687159296 |
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| author | Liam S. Fitzgerald Ciaran O’Malley Paul V. Murphy |
| author_facet | Liam S. Fitzgerald Ciaran O’Malley Paul V. Murphy |
| author_sort | Liam S. Fitzgerald |
| collection | DOAJ |
| description | Treatment of <i>N</i>-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single crystal X-ray diffraction analysis, as well as FT-IR, NMR spectroscopic and HRMS analysis. |
| first_indexed | 2024-03-09T13:12:30Z |
| format | Article |
| id | doaj.art-53866e243bcc486f8becbac27e3c17ef |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T13:12:30Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-53866e243bcc486f8becbac27e3c17ef2023-11-30T21:39:37ZengMDPI AGMolbank1422-85992022-02-0120221M133710.3390/M1337(1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl AcetateLiam S. Fitzgerald0Ciaran O’Malley1Paul V. Murphy2School of Biological and Chemical Sciences, National University of Ireland Galway, University Road, H91 TK33 Galway, IrelandSchool of Biological and Chemical Sciences, National University of Ireland Galway, University Road, H91 TK33 Galway, IrelandSchool of Biological and Chemical Sciences, National University of Ireland Galway, University Road, H91 TK33 Galway, IrelandTreatment of <i>N</i>-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single crystal X-ray diffraction analysis, as well as FT-IR, NMR spectroscopic and HRMS analysis.https://www.mdpi.com/1422-8599/2022/1/M1337sialic acidN-acetylneuraminic acid1,4 lactonesγ-lactonespolyhydroxylated compounds |
| spellingShingle | Liam S. Fitzgerald Ciaran O’Malley Paul V. Murphy (1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate Molbank sialic acid N-acetylneuraminic acid 1,4 lactones γ-lactones polyhydroxylated compounds |
| title | (1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate |
| title_full | (1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate |
| title_fullStr | (1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate |
| title_full_unstemmed | (1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate |
| title_short | (1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate |
| title_sort | 1 i r i 2 i r i 3 i s i 4 i r i 1 acetylamino 2 4 5 tris acetyloxy 1 2 i s i 4 benzyloxy 5 oxo 2 5 dihydrofuran 2 yl pentan 3 yl acetate |
| topic | sialic acid N-acetylneuraminic acid 1,4 lactones γ-lactones polyhydroxylated compounds |
| url | https://www.mdpi.com/1422-8599/2022/1/M1337 |
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