Synthesis of 06-Alkylated Guanosine and Deoxyguanosinephosphoramidites

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Abstract
Since 06-alkylguanine derivatives play a specific role in nucleic acids as potential sources o f mutagenic (1) and carcinogenic (2) action the monomeric building blocks of this type of compounds are desirable for more detailed studies. The old route to 06-alkyl ribonucleosides via the corresponding 6-chloro derivative worked with low yields in the 2′-deoxy series and could only just recently be improved by functionalizing the amide group first by sulfonylation on oxygen and followed by subsequent displacement of trimethylamine and various alkoxides (3).