Unexpected dehalogenation of 3-bromopyrazolo[3,4-d]pyrimidine nucleosides during nucleobase-anion glycosylation

Autor(en): Seela, F
Zulauf, M
Becher, G
Stichwörter: 2'-DEOXYRIBOFURANOSIDES; AGENT; ALLOPURINOL; ANALOGS; Biochemistry & Molecular Biology; BIOLOGICAL-ACTIVITY; DNA
Erscheinungsdatum: 1997
Herausgeber: MARCEL DEKKER INC
Journal: NUCLEOSIDES & NUCLEOTIDES
Volumen: 16
Ausgabe: 3
Startseite: 305
Seitenende: 314
Zusammenfassung: 
The anion-glycosylation (KOH, MeCN, TDA-1) of 3-bromopyrazolo[3,4-d]pyrimidines 4a and 4b with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranoysl chloride (5) furnishes the regioisomeric N-1-beta-D-2'-deoxyribonucleosides 6a and 6b together with the dehalogenated N-2-regioisomers 8a and 8b, stereoselectively. The dehalogenation takes place after the glycosylation and results from the sensitivity of the N-2 nucleosides toward aqueous base. An addition/elimination mechanism is suggested for the dehalogenation reaction.
ISSN: 07328311
DOI: 10.1080/07328319708001351

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