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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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Published in: | Journal of organic chemistry 2018-08, Vol.83 (15), p.8589-8595 |
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Main Authors: | , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b00343 |