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.
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.
Leonard
Peter
P
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Munster, Germany.
Ingale
Sachin A
SA
Ding
Ping
P
Ming
Xin
X
Seela
Frank
F
D006031:Glycosylation; D007288:Inosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D014127:Toyocamycin / Q000138:chemical synthesis*
D011743:Pyrimidines; D011758:Pyrroles; D007288:Inosine; C049047:7-deazainosine; D014127:Toyocamycin