459839-20-4Relevant academic research and scientific papers
Synthesis of nucleosides from 4-methylidenefuranoses: A non-classical electrophilic addition
Robles, Rafael,Izquierdo, Isidoro,Rodriguez, Concepcion,Plaza, Maria T.,Mota, Antonio J.,Alvarez de Cienfuegos, Luis
, p. 399 - 405 (2002)
The reaction of persilylated bases (thymine, uracil, cytosine, and 5-fluorouracil) with either 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-erythro-pent-4-enofuranose 6 or its 3-O-benzyl analogue 7 in the presence of N-iodosuccinimide (NIS) afforded two types of product with high stereoselectivity; either (1′S,2′R,3′S)-3′-O-benzoyl- 8-10 or -3′-O-benzyl-5′-deoxy-5′-iodo-1′,2′-O- isopropylidene-4′-oxo-1′-yl-pyrimidines 11-13, respectively, from 1,4-addition with participation of the oxygen atom at the furanoid ring, and either 3′-O-benzoyl- 14-16, or 3′-O-benzyl-5′-deoxy-5′-iodo-1′,2′-O- isopropylidene-β-L-lyxo-4′-yl-pyrimidine and 17-19 resulting from normal electrophilic addition at the exocyclic methylene group. A third compound was isolated from the reaction of 7 with persilylated uracil/NIS and identified as the doubly N,N′-glycosylated pyrimidine 20.
