Stereocontrolled approach for the syntheses of 3-isopurine nucleosides: 3-(2-deoxy-β-d-ribofuranosyl)xanthine and isoguanine by intramolecular glycosylation. Issue 44 (28th October 2015)

• Record Type: Journal Article
• Authors: Sugimura, Hideyuki; Endo, Sho; Ishizuka, Ken
• Is Part Of: Tetrahedron letters. Volume 56:Issue 44(2015)
• Page Start: 6019
• Page End: 6021
• Publication Date: 2015-10-28
• Subjects: 3-Isopurine nucleoside -- Intramolecular glycosylation -- 2′-Deoxy-3-isoxanthine -- 3-(2-Deoxyribosyl)isoguanine -- Stereoselective reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.045
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 3-Isopurine nucleosides, namely 3-(ribofuranosyl)purine nucleosides, are interesting owing to their potential biological activity and as components of modified oligonucleotides. A regio- and stereocontrolled method was developed for the synthesis of β-2′-deoxy-3-isopurine nucleosides using the intramolecular glycosylation protocol. The availability of this method was shown by the first chemical synthesis of 3-(2-deoxy-β-d -ribofuranosyl)xanthine and isoguanine.