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

Show full item record

Page view(s)

1
Last Week
0
Last month
0
checked on Mar 2, 2024

Google ScholarTM

Check

Altmetric