IUCr journals

1-(1-Carboxymethyl-1,4-anhydro-2,3-O-isopropylidene-α-d-erythrofuranosyl)thymine

Acta Cryst. (2010). E66, o404 (doi.org/10.1107/S1600536810001704)

[Nucleoside scheme]

Psicofuranine is a naturally occurring branched-sugar nucleoside which exhibits potent biological activity; however, it is cardiotoxic to man. In studies to synthesise analogues of psicofuranine and evaluate their biological potential, methodology was developed to introduce the nucleoside base via a Vorbrüggen-type displacement on a carbohydrate-derived α-bromoester. α/β selectivity is extremely important for biological activity and X-ray crystallography has been invaluable to unequivocally assign the stereochemistry of the nucleoside base.

G. M. J. Lenagh-Snow, S. F. Jenkinson, A. J. Stewart, G. W. J. Fleet and D. J. Watkin