Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-Nucleosides
Glycosylation of 6-(2) and 7-p-bromophenyllumazine (3) by the silyl method using 1-O-acetyl-2.3 ,5-tri-O-benzoyl-β-D-ribofuranose (6) and trimethylsilyl trifluoromethanesulfonate as catalyst proceeded regioselectively in high yields to the N-1 nucleosides (7, 11). Thiations by P4S10 or Lawesson’s re...
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| Format: | Article |
| Language: | English |
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De Gruyter
1990-01-01
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| Series: | Pteridines |
| Online Access: | https://doi.org/10.1515/pteridines.1990.2.1.9 |
| _version_ | 1831761891603513344 |
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| author | Al-Masoudi Najim A. L. Pfleiderer Wolfgang |
| author_facet | Al-Masoudi Najim A. L. Pfleiderer Wolfgang |
| author_sort | Al-Masoudi Najim A. L. |
| collection | DOAJ |
| description | Glycosylation of 6-(2) and 7-p-bromophenyllumazine (3) by the silyl method using 1-O-acetyl-2.3 ,5-tri-O-benzoyl-β-D-ribofuranose (6) and trimethylsilyl trifluoromethanesulfonate as catalyst proceeded regioselectively in high yields to the N-1 nucleosides (7, 11). Thiations by P4S10 or Lawesson’s reagent led to the corresponding 4-thiolumazine ribosides (9, 13). Deblocking to the free nucleosides (8, 10, 12. 14) worked best with K2CO3, in MeOH. Treatment of 9 and 13 respectively by methanolic NH3 afforded debenzoylation and di splacement of the thio-function to give the corresponding isopterin N-1 ribofuranosides (15.16). 2,2ʹ-Anhydro- nucleoside formation was achieved with 8 and 10 respectively to give 17 and 18, which formed on acid hydrolysis the 6- and 7-substituted l-~-D-arabinofuranosyl-lumazines 19 and 20. |
| first_indexed | 2024-12-22T04:57:06Z |
| format | Article |
| id | doaj.art-510a3b1b00524210bb4f50dceebb30b0 |
| institution | Directory Open Access Journal |
| issn | 0933-4807 2195-4720 |
| language | English |
| last_indexed | 2024-12-22T04:57:06Z |
| publishDate | 1990-01-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Pteridines |
| spelling | doaj.art-510a3b1b00524210bb4f50dceebb30b02022-12-21T18:38:21ZengDe GruyterPteridines0933-48072195-47201990-01-012191510.1515/pteridines.1990.2.1.9Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-NucleosidesAl-Masoudi Najim A. L.0Pfleiderer Wolfgang1Dept. of Chemistry, College of Science, University of Basrah, Basrah, IraqFakultät für Chemie, Universität Konstanz, Postfach 5560, 0-77 50 Konstanz. Federal Republic of GermanyGlycosylation of 6-(2) and 7-p-bromophenyllumazine (3) by the silyl method using 1-O-acetyl-2.3 ,5-tri-O-benzoyl-β-D-ribofuranose (6) and trimethylsilyl trifluoromethanesulfonate as catalyst proceeded regioselectively in high yields to the N-1 nucleosides (7, 11). Thiations by P4S10 or Lawesson’s reagent led to the corresponding 4-thiolumazine ribosides (9, 13). Deblocking to the free nucleosides (8, 10, 12. 14) worked best with K2CO3, in MeOH. Treatment of 9 and 13 respectively by methanolic NH3 afforded debenzoylation and di splacement of the thio-function to give the corresponding isopterin N-1 ribofuranosides (15.16). 2,2ʹ-Anhydro- nucleoside formation was achieved with 8 and 10 respectively to give 17 and 18, which formed on acid hydrolysis the 6- and 7-substituted l-~-D-arabinofuranosyl-lumazines 19 and 20.https://doi.org/10.1515/pteridines.1990.2.1.9 |
| spellingShingle | Al-Masoudi Najim A. L. Pfleiderer Wolfgang Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-Nucleosides Pteridines |
| title | Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-Nucleosides |
| title_full | Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-Nucleosides |
| title_fullStr | Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-Nucleosides |
| title_full_unstemmed | Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-Nucleosides |
| title_short | Nucleosides, XLVII. Syntheses, Reactions and Properties of 6- and 7-p-Bromophenyllumazine N-1-Nucleosides |
| title_sort | nucleosides xlvii syntheses reactions and properties of 6 and 7 p bromophenyllumazine n 1 nucleosides |
| url | https://doi.org/10.1515/pteridines.1990.2.1.9 |
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