STUDIES ON THE GLYCOSYLATION OF PYRROLO[2,3-d] PYRIMIDINES WITH 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-beta-D-RIBOFURANOSE: THE FORMATION OF REGIOISOMERS DURING TOYOCAMYCIN AND 7-DEAZAINOSINE SYNTHESES
| Autor(en): | Leonard, Peter Ingale, Sachin A. Ding, Ping Ming, Xin Seela, Frank |
Stichwörter: | 3-d]pyrimidines; 7-deazainosine; ACID RELATED-COMPOUNDS; Biochemistry & Molecular Biology; ECHIGUANINE-A; EFFICIENT SYNTHESIS; glycosylation; MYCALISINE-A; NMR-spectra; NUCLEOSIDE ANTIBIOTICS; Nucleosides; PHASE-TRANSFER GLYCOSYLATION; PRACTICAL SYNTHESIS; PYRROLO<2,3-D>PYRIMIDINE NUCLEOSIDES; pyrrolo[2; PYRROLOPYRIMIDINE NUCLEOSIDES; RIBOFURANOSYL CHLORIDES; toyocamycin | Erscheinungsdatum: | 2009 | Herausgeber: | TAYLOR & FRANCIS INC | Journal: | NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | Volumen: | 28 | Ausgabe: | 5-7, SI | Startseite: | 678 | Seitenende: | 694 | Zusammenfassung: | Glycosylation of silylated 4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidine (9) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (10) under ``one-pot'' glycosylation conditions (MeCN, TMSOTf) yielded the N-7 isomer 11 together with the N-1 compound 13 (ratio = 2:1). When the same conditions were applied to 4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine (21) the N-3 isomer 22 was the only glycosylation product formed in almost quantitative yield. |
ISSN: | 15257770 | DOI: | 10.1080/15257770903091953 |
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geprüft am 01.06.2024
