Synthesis of 2′-Deoxy-2′-C-α-methylpurine Nucleosides

Abstract

2′-Deoxy-2′-C-α-methylribonucleosides provide valuable biochemical probes with which to study RNA structure and function. Using methyl 2-acetoxymethyl-3,5-di-O-(tert-butyldi­methylsilyl)-d-ribofuranoside (1) as a glycosylating agent, we achieved in four steps an improved synthesis of 2′-deoxy-2′-C-α-methyladenosine (8) and the first synthesis of 2′-deoxy-C-α-methylguanosine (9) in 25% and 17% overall yield, respectively.

Key words

nucleosides - deoxygenation - glycosylation - deoxy­methyladenosine - deoxymethylguanosine

References

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