Original scientific paper

The Homologation of 1-(2,3-Dihydroxypropyl)- into 1-(2,4-Dihydroxyhutyl)-thymine

V . Škarić ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« Institute, 41001 Zagreb, Croatia, Yugoslavia
Z. Raza ; Laboratory of Stereochemistry and Natural Products, »Ruder Boskovic« Institute, 41001 Zagreb, Croatia, Yugoslavia

Abstract

The homologation of 1-(2,3-dihydroxypropyl)thymine involved
the conversion of its 3'-0-tosyl derivative II into the corresponding
3'-iodo compound IV, which by nucleophilic displacement with
sodium cy,anide in DMSO formed 1-(2-hydroxy-3-cyanopropyl)
thymine (VIII). 1-(2,3-Dihydroxypropyl)uracil was analogously converted
into the corresponding 3'-iodo- III and 3'-cyano- VII propyluracil.
The ethanolysis of the 3'-cyano compound VIII to 1-(2-
-hydroxy-3-ethoxycarbonylpropyl)thymine (X), followed by the
reduction with LiAlH4, gave 1-(2,4-dihydroxybutyl)thymine (XIII).
3'-0-Acetylthymidylyl(5'~2')-1-(4-0-triphenylmethyl-2,4-dihydroxybutyl)
thymine was described as possible N,N-dicyclohexylpseudourea
adduct XIX.

Keywords

Hrčak ID:

195914

URI

https://hrcak.srce.hr/195914

Publication date:

19.4.1979.

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