7-Functionalized 7-deazapurine beta-D and beta-L-ribonucleosides related to tubercidin and 7-deazainosine: glycosylation of pyrrolo[2,3-d] pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D or beta-L-ribofuranose
Autor(en): | Seela, Frank Ming, Xin |
Stichwörter: | `one-pot' glycosylation; ANALOGS; ANTIVIRAL ACTIVITY; Chemistry; Chemistry, Organic; cross-coupling; DNA; GENERAL-SYNTHESIS; halogenated 7-deazapurines; N BOND FORMATION; OLIGONUCLEOTIDES; PHASE-TRANSFER GLYCOSYLATION; pK(a) values; PYRROLOPYRIMIDINE NUCLEOSIDES; ribonucleosides; RNA; TOYOCAMYCIN | Erscheinungsdatum: | 2007 | Herausgeber: | PERGAMON-ELSEVIER SCIENCE LTD | Journal: | TETRAHEDRON | Volumen: | 63 | Ausgabe: | 39 | Startseite: | 9850 | Seitenende: | 9861 | Zusammenfassung: | Several 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of 7-halogenated 6-chloro-7-deazapurines with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose or 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-L-ribofuranose gave the protected beta-D-nucleosides 8c-e (53-62%) and the beta-L-nucleosides 9b-e (57-72%), which were transformed to 7-halogenated 7-deazapurine ribonucleosides related to tubercidin and 7-deazainosine. 7-Alkynyl derivatives (1f,g) and (2f,g) were obtained from the 7-iodo nucleosides 1e and 2e employing the palladium-catalyzed Sonogashira cross-coupling reaction. Within the series of 7-deazaadenosine ( tubercidin) analogues and 7-deazainosine derivatives physical data such as pK(a) values, chromatographic mobilities, C-13 NMR chemical shifts were determined and correlated to each other. (C) 2007 Elsevier Ltd. All rights reserved. |
ISSN: | 00404020 | DOI: | 10.1016/j.tet.2007.06.107 |
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geprüft am 18.05.2024