The synthesis of 4-deazaformycin A.
The preparation of 4-deazaformycin A has been achieved. The synthesis features the condensation of a suitably substituted, lithiated 4-picoline with 2,3,5-tri-O-benzyl-d-ribonolactone, dehydration of the resulting hemiacetal, and ionic hydrogenation, followed by manipulation of the protecting groups and subsequent ring closure with the formation of 7-amino-3-(beta-d-ribofuranosyl)pyrazolo[3,4-c]pyridine.
Kourafalos
Vassilios N
VN
Department of Pharmacy, Division of Pharmaceutical Chemistry, University of Athens, Panepistimiopolis Zografou 15771, Athens, Greece.
Marakos
Panagiotis
P
Pouli
Nicole
N
Townsend
Leroy B
LB
D002855:Chromatography, Thin Layer; D005573:Formycins / Q000138:chemical synthesis*; D005663:Furans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011720:Pyrazoles / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism
C481906:5-deazaformycin A; D005573:Formycins; D005663:Furans; D007202:Indicators and Reagents; D011720:Pyrazoles; D011725:Pyridines; C118531:pyrazolopyridine; C018674:tetrahydrofuran