Collect. Czech. Chem. Commun. 1989, 54, 1055-1066

Use of 5-deoxy-ribo-hexofuranose derivatives for the preparation of 5'-nucleotide phosphonates and homoribonucleosides

Sergei N. Mikhailov, Nelly Sh. Padyukova, Marat Ya. Karpeiskii, Lidiya I. Kolobushkina and Leon N. Beigelman

Institute of Molecular Biology, The USSR Academy of Sciences, 117984 Moscow, U.S.S.R.


A convenient and general method is proposed for the synthesis of 5'-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose which can easily be produced in preparative quantities from D-glucose. Phosphonate IIIe was synthesized by means of the Arbuzov reaction between 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose and triethyl phosphite. The consecutive acetolysis, condensation with uracil and N6-benzoyladenine bis-trimethylsilyl derivatives and deblocking possessed phosphonate analogs of 5'-nucleotides in good yields. The intermediate 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose derivatives were used for the preparation of homonucleosides.