The synthesis of nebularine and its analogs via oxidative desulfuration in aqueous nitric acid. (2nd January 2017)

• Record Type: Journal Article
• Authors: Xia, Ran; Sun, Li-Ping; Qu, Gui-Rong
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 192:Number 1(2017)
• Page Start: 88
• Page End: 91
• Publication Date: 2017-01-02
• Subjects: Nebularine -- desulfuration -- base modification -- nucleoside synthesis; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2016.1225057
• Languages: English
• ISSNs: 1042-6507

Abstract

GRAPHICAL ABSTRACT: ABSTRACT: The synthesis of nebularine and its analogs has been achieved via oxidative desulfuration in H2 O for the first time. With 50% HNO3 as an oxidant and solvent, 18 products were obtained in good yields (70%–94%). The oxidative desulfuration system could tolerate different functional groups including fluoro, chloro, amino, alkyl, allyl, ribosyl, deoxyribosyl, and arabinofuranosyl groups. More importantly, the drug nebularine could be obtained successfully on a 20 g scale, which made this route more attractive for industrial applications.