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Short Paper | Special issue | Vol 88, No. 2, 2014, pp.1491-1499
Published online, 19th August, 2013
DOI: 10.3987/COM-13-S(S)47
Selective Preparation of 6- and 7-(Polyhydroxypropyl)pterins from Pentos-2-uloses

Tadashi Hanaya* and Kasumi Ito

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


The Gabriel-Isay condensation of three types of pentos-2-uloses with 2,5,6-triaminopyrimidin-4(3H)-one (3) was examined under both acidic and basic conditions. The condensation of 5-deoxy- and 5-O-protected pentofuranos-2-uloses with 3 at pH 8 afforded 6-substituted pterins as major isomers, whereas the same reaction at pH 3 yielded the 7-substituted pterins predominantly.