134660-08-5Relevant academic research and scientific papers
Nitrogen glycosylation reactions involving pyrimidine and purine nucleoside bases with furanoside sugars
Wilson,Hager,El-Kattan,Liotta
, p. 1465 - 1479 (2007/10/02)
Different approaches for the synthesis of nucleoside analogs (potential HIV inhibitors) are described. Starting from a suitably substituted furanose ring, it is demonstrated that a high facial stereocontrol of the glycosylation reaction can be effected. Different reaction conditions including Lewis acid promoted, S(N)2 displacement and some enzymatic methodologies for the stereoselective synthesis of these compounds are reviewed.
Synthesis of 2'-azido, 2,2'-anhydro and 2',5'-anhydro nucleosides with potential anti-HIV activity
Abdel-Megied,Pedersen,Nielsen
, p. 313 - 317 (2007/10/02)
Reaction of methyl 2-bromo-2,3-dideoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside (7) with silylated uracils 9 using trimethylsilyl triflate as catalyst afforded the corresponding 2'-bromonucleosides 10. 2,3-Didehydro sugar 8 was prepared by heating 7 with sodium azide in dimethylformamide. 2,2'-Anhydronucleosides 1 were prepared by treating the nucleosides 10 with sodium methoxide at room temperature. 1-(2-Azido-2,3-dideoxy-β-D-threo-pentofuranosyl)thymine (15) and its α-anomer (16) were prepared by treating 10c with sodium azide and subsequently methanolic ammonia. Treatment of 1-(2-bromo-2,3-dideoxy-α-D-erythro-pentofuranosyl)thymine (11c) with excess of sodium methoxide under reflux gave the corresponding 2',5'-anhydro nucleoside 17.
