Regioselective synthesis of indazole N-1- and N-2-(beta-D-ribonucleosides)

Autor(en): Seela, F
Peng, XH
Stichwörter: 4-nitroindazole; Biochemistry & Molecular Biology; fluorescence; GLYCOSYLATION; NUCLEOSIDES; regioselectivity; RIBOFURANOSYLINDAZOLES; ribonucleosides
Erscheinungsdatum: 2004
Herausgeber: MARCEL DEKKER INC
Journal: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Volumen: 23
Ausgabe: 1-2
Startseite: 227
Seitenende: 237
Zusammenfassung: 
The regioselective synthesis of 4-nitroindazole N-1- and N-2- (beta-D-ribonucleosides) (8, 9, 1b and 2b) is described. The N-1-regioisomers are formed under thermodynamic control of the glycosylation reaction [fusion reaction or Silyl Hilbert-Johnson glycosylation for 48 h (66%)], while the kinetic control (Silyl Hilbert-Johnson glycosylation for 5 h) afforded only the N-2-isomer (64%). The structures of the nucleosides 1b and 2b were assigned by single crystal X-ray analyses. The 4-amino-N-1-(beta-D-ribofuranosyl)-1H-indazole (3b) was obtained from the nitro nucleoside 1b by catalytic hydrogenation. Compound 3b shows fluorescence while the 4-nitroindazole nucleosides 1b and 2b do not possess this property.
ISSN: 15257770
DOI: 10.1081/NCN-120027830

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