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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