A Facile Synthesis of 3 ′-Fluoro Hexitol Adenosine and Guanosine Phosphoramidites

We report a convenient and scalable synthetic approach for the synthesis of 3′-fluoro hexitol adenosine and guanosine nucleoside analogues and corresponding phosphoramidites in good yield. 1,5-Anhydro-4,6-O-benzylidene-d-glucitol was converted into 1,5-anhydro-4,6-O-benzylidene-3-deoxy-3-fluoro-2-O-trifluoromethanesulfonyl-d-altritol in a three-step process. Glycosylation using adenosine or 2-amino-6-iodopurine yielded the corresponding nucleoside analogues in excellent yield. Based on this strategy, a highly concise and scalable synthesis of 3′-fluoro hexitol purine nucleosides (1–2 g, 18–21% overall yield) was accomplished, which will enable the use of 3′-fluoro hexitol nucleic acids for genetic medicine development and diagnostic applications. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - October 19, 2023 Category: Chemistry Authors: Prakash, Thazha P. Yu, Jinghua Vasquez, Guillermo Allerson, Charels R. Swayze, Eric E. Tags: cluster Source Type: research