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

Article abstract of DOI:10.1080/07328319708001351

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)-α-D-erythro- pentofuranosyl chloride (5) furnishes the regioisomeric N¹-β-D-2'- deoxyribonucleosides 6a and 6b together with the dehalogenated N²- 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.

Full text of DOI:10.1080/07328319708001351

Nucleosides and Nucleotides
ISSN: 0732-8311 (Print) (Online) Journal homepage: http://www.tandfonline.com/loi/lncn19
Unexpected Dehalogenation of 3-
Bromopyrazolo[3,4-d]pyrimidine Nucleosides
During Nucleobase-Anion Glycosylation
Frank Seela , Matthias Zulauf & Georg Becher
To cite this article: Frank Seela , Matthias Zulauf & Georg Becher (1997) Unexpected
Dehalogenation of 3-Bromopyrazolo[3,4-d]pyrimidine Nucleosides During Nucleobase-Anion
Glycosylation, Nucleosides and Nucleotides, 16:3, 305-314, DOI: 10.1080/07328319708001351
To link to this article: http://dx.doi.org/10.1080/07328319708001351
Published online: 22 Aug 2006.
Submit your article to this journal
Article views: 35
View related articles
Citing articles: 5 View citing articles
Full Terms & Conditions of access and use can be found at
http://www.tandfonline.com/action/journalInformation?journalCode=lncn20
Download by: [RMIT University]
Date: 25 January 2016, At: 04:19