Synthesis of uracil polyoxin C from uridine

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Abstract

An improved procedure is reported for the asymmetric synthesis of uracil polyoxin C (UPOC) from 2',3'-O-isopropylideneuridine-5'-aldehyde. The methodology described here is based on the highly diastereocontrolled formation of 1-(β-D-allofuranosyl)uracil and its facile conversion into the corresponding 2,5'-O-cyclouridine derivative, a key step for the stereocontrolled formation of the terminal α-amino acid of UPOC.

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Evina, C. M., & Guillerm, G. (1996). Synthesis of uracil polyoxin C from uridine. Tetrahedron Letters, 37(2), 163–166. https://doi.org/10.1016/0040-4039(95)02116-7

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