7-functionalized 7-deazapurine ribonucleosides related to 2-aminoadenosine, guanosine, and xanthosine: Glycosylation of pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose
Autor(en): | Seela, F Peng, XH |
Stichwörter: | ANTIBIOTIC TOYOCAMYCIN; ANTIVIRAL ACTIVITY; Chemistry; Chemistry, Organic; CONFORMATIONAL-ANALYSIS; N BOND FORMATION; OLIGONUCLEOTIDE DUPLEXES; PHASE-TRANSFER GLYCOSYLATION; PYRROLO<2,3-D>PYRIMIDINE NUCLEOSIDES; PYRROLOPYRIMIDINE NUCLEOSIDES; RIBOFURANOSYL CHLORIDES; STEREOSELECTIVE-SYNTHESIS | Erscheinungsdatum: | 2006 | Herausgeber: | AMER CHEMICAL SOC | Journal: | JOURNAL OF ORGANIC CHEMISTRY | Volumen: | 71 | Ausgabe: | 1 | Startseite: | 81 | Seitenende: | 90 | Zusammenfassung: | The Silyl-Hilbert-Johnson reaction as well as the nucleobase-anion glycosylation of a series of 7-deazapurines has been investigated, and the 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of the 7-halogenated 6-chloro-2-pivaloylamino-7-deazapurines 9b-d with 1-O-acetyl2,3,5-tri-O-benzOyl-D-ribofuranose (5) gave the beta-D-nucleosides 11b-d (73-75% yield), which were transformed to a number of novel 7-halogenated 7-deazapurine ribonucleosides (2b-d, 3b-d, and 4b-d) related to guanosine, 2-aminoadenosine, and xanthosine. 7-Alkynyl derivatives (2e-i, 3e-h, or 4g) have been prepared from the corresponding 7-iodonucleosides 2d, 3d, or 4d employing the palladium-catalyzed Sonogashira cross-coupling reaction. The 7-halogenated 2-amino-7-deazapurine ribonucleosides with a reactive 6-chloro substituent (18b-d) were synthesized in an alternative way using nucleobase-anion glycosylation performed on the 7-halogenated 2-arnino-6-chloro-7-deazapurines 13b-d with 5-0-[(1,1dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-alpha -D-ribofuranosyl chloride (17). Compounds 18b-d have been converted to the nucleosides 19b-d carrying reactive substituents in the pyrimidine moiety. Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution. |
ISSN: | 00223263 | DOI: | 10.1021/jo0516640 |
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geprüft am 18.05.2024