Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR Analysis
Abstract The reactivity of trifluoromethanesulfonyl esters derived from l-lyxofuranosides and l-lyxopyranosides was investigated with various 5-aminopyrimidines as nucleophiles with the expectation to synthesize N-substituted 5-amino-ribosugars. The lyxopyranoside forms were found to be unreactive,...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Georg Thieme Verlag KG
2017-03-01
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| Series: | SynOpen |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1588859 |
| _version_ | 1828395519129419776 |
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| author | Alba Diez-Martinez Ramanarayanan Krishnamurthy |
| author_facet | Alba Diez-Martinez Ramanarayanan Krishnamurthy |
| author_sort | Alba Diez-Martinez |
| collection | DOAJ |
| description | Abstract
The reactivity of trifluoromethanesulfonyl esters derived from l-lyxofuranosides and l-lyxopyranosides was investigated with various 5-aminopyrimidines as nucleophiles with the expectation to synthesize N-substituted 5-amino-ribosugars. The lyxopyranoside forms were found to be unreactive, while the lyxofuranoside forms were found to be reactive with 5-aminopyrimidines, yielding novel N-substituted 5-amino-lyxofuranosides. We report on the synthesis of these novel N-substituted lyxofuranosides and the systematic analyses of NMR data that demonstrate trends within each series: furano-, pyrano-, β- and α- anomers of l-lyxose and β-d-ribopyranoside forms. The data call for caution when identifying these monosaccharides in isomeric mixtures. |
| first_indexed | 2024-12-10T08:14:29Z |
| format | Article |
| id | doaj.art-20176fceeae14d17b68f02f233111b06 |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-12-10T08:14:29Z |
| publishDate | 2017-03-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-20176fceeae14d17b68f02f233111b062022-12-22T01:56:30ZengGeorg Thieme Verlag KGSynOpen2509-93962017-03-0101010029004010.1055/s-0036-1588859Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR AnalysisAlba Diez-MartinezRamanarayanan KrishnamurthyAbstract The reactivity of trifluoromethanesulfonyl esters derived from l-lyxofuranosides and l-lyxopyranosides was investigated with various 5-aminopyrimidines as nucleophiles with the expectation to synthesize N-substituted 5-amino-ribosugars. The lyxopyranoside forms were found to be unreactive, while the lyxofuranoside forms were found to be reactive with 5-aminopyrimidines, yielding novel N-substituted 5-amino-lyxofuranosides. We report on the synthesis of these novel N-substituted lyxofuranosides and the systematic analyses of NMR data that demonstrate trends within each series: furano-, pyrano-, β- and α- anomers of l-lyxose and β-d-ribopyranoside forms. The data call for caution when identifying these monosaccharides in isomeric mixtures.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1588859 l-lyxofuranoses l-lyxopyranoses d-ribopyranosesconformation analysisheterocyclesnmr spectroscopy |
| spellingShingle | Alba Diez-Martinez Ramanarayanan Krishnamurthy Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR Analysis SynOpen l-lyxofuranoses l-lyxopyranoses d-ribopyranoses conformation analysis heterocycles nmr spectroscopy |
| title | Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR Analysis |
| title_full | Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR Analysis |
| title_fullStr | Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR Analysis |
| title_full_unstemmed | Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR Analysis |
| title_short | Investigations towards the Synthesis of 5-Amino-l-lyxofuranosides and 4-Amino-lyxopyranosides and NMR Analysis |
| title_sort | investigations towards the synthesis of 5 amino l lyxofuranosides and 4 amino lyxopyranosides and nmr analysis |
| topic | l-lyxofuranoses l-lyxopyranoses d-ribopyranoses conformation analysis heterocycles nmr spectroscopy |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1588859 |
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