Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis

Add time:07/17/2019    Source:sciencedirect.com

D-Altritol nucleosides with an adenine and uracil base moiety were obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol using the sodium salt of the above mentioned bases. The use of a 2-trimethylsilylethyl protecting group for the O6-function of the guanine base offers a useful compromise between stability and acceptable alkylation yields of the N9-position if the guanine base. The cytosine nucleoside was synthesized starting from the uracil congener. The 3′-hydroxyl function was protected with a benzoyl group.

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