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Nucleic Acids Research, 1990, Vol. 18, No. 1 41-49
© 1990

CHEMISTRY

New synthetic routes to protected purine 2'-O-methylriboside-3'-O-phosphoramidites using a novel alkylation procedure

Brian S. Sproat, Barbro Beijer* and Adolfo Iribarren

European Molecular Biology Laboratory Postfach 10.2209, D-6900 Heidelberg, FRG

* To whom correspondence should be addressed

Received October 27, 1989. Accepted December 1, 1989.

A highly selective alkylation procedure has been developed enabling new synthetic routes to be established for protected purine 2'-O-methylriboside- 3'-O-phosphoramidites; building blocks for the assembly of 2'-O-methyloligoribonucleotides. The new procedure avoids the use of the highly toxic and potentially explosive reagent diazomethane and is far superior to the use of silver oxide/methyl iodide. Moreover, the use of highly versatile key intermediates will enable the synthesis of a wide variety of base modified analogues as well as other 2'-O-alkylriboside derivatives.


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