Glycosylation of Pyrrolo[2,3-d]pyrimidines with 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose: Substituents and Protecting Groups Effecting the Synthesis of 7-Deazapurine Ribonucleosides

Autor(en): Ingale, Sachin A.
Leonard, Peter
Seela, Frank
Stichwörter: 7-DEAZAINOSINE; Chemistry; Chemistry, Organic; DERIVATIVES; DNA; N-15-NMR SPECTRA; NUCLEOSIDE-Q; PCR; PHASE-TRANSFER GLYCOSYLATION; PYRROLOPYRIMIDINE NUCLEOSIDES; REGIOSELECTIVE SYNTHESES; TUBERCIDIN
Erscheinungsdatum: 2018
Herausgeber: AMER CHEMICAL SOC
Journal: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 83
Ausgabe: 15
Startseite: 8589
Seitenende: 8595
Zusammenfassung: 
Glycosylation of nonfunctionalized 6-chloro-7-deazapurine with commercially available 1-0-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (45%) followed by amination and deprotection gave tubercidin in only two steps. Similar conditions applied for the synthesis of 7-deazaguanosine employing pivaloylated 2-amino-6-chloro-7-deazapurine gave 18% glycosylation yield. The less bulky isobutyryl or acetyl protected amino group directed the glycosylation toward the exocyclic amino substituent. 7-Halogenated intermediates were glycosylated followed by dehalogenation to overcome the low glycosylation yield in the synthesis of 7-deazaguanosine.
ISSN: 00223263
DOI: 10.1021/acs.joc.8b00343

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