2,5-Anhydro-1-deoxy-1-phosphono-D-altritol, an isosteric analog of .alpha.-D-ribofuranose 1-phosphate

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Abstract
Condensation of tetramethyl methylenebisphosphonate with 2,3-O-isopropylidene-5-O-trityl-D-ribose gave a mixture of 2,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-2,3 -O-isopropylidene-5-O-trityl-D-altritol and -allitol. Separation of the isomers and deprotection gave 2,5-anhydro-1-deoxy-1-phosphono-D-altritol and -allitol. The former is the stable isosteric methylenephosphonate analogue of alpha-D-ribose 1-phosphate, the ribose donor in nucleoside phosphorylase catalyzed nucleoside biosynthetic reactions. It did not, however, inhibit purine nucleoside phosphorylase at concentrations of 6 mM.

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