Studies on the Glycosylation of Pyrrolo [2, 3-d] Pyrimidines with 1-O-Acetyl-2, 3, 5-Tri-O-Benzoyl-β-D-Ribofuranose: The Formation of Regioisomers During …

P Leonard, SA Ingale, P Ding, X Ming…

文献索引：Leonard, Peter; Ingale, Sachin A.; Ding, Ping; Ming, Xin; Seela, Frank Nucleosides, Nucleotides and Nucleic Acids, 2009 , vol. 28, # 5-7 p. 678 - 694

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被引用次数: 6

摘要

Glycosylation of silylated 4-amino-6-bromo-5-cyano-7 H-pyrrolo [2, 3-d] pyrimidine (9) with 1- O-acetyl-2, 3, 5-tri-O-benzoyl-β-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-7 H-pyrrolo [2, 3-d] pyrimidine (21) the N-3 isomer 22 was the only glycosylation product formed in almost quantitative yield.