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

Glycosylation of nonfunctionalized 6-chloro-7-deazapurine with commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (45%) followed by amination and deprotection gave tubercidin in only two steps. Similar conditions applied for the synthesis of 7-deazaguanosine employing pivaloylate...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-08, Vol.83 (15), p.8589-8595
Main Authors: Ingale, Sachin A, Leonard, Peter, Seela, Frank
Format: Article
Language:English
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Summary:Glycosylation of nonfunctionalized 6-chloro-7-deazapurine with commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-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:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00343