Journal
TETRAHEDRON LETTERS
Volume 43, Issue 5, Pages 795-797Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)02274-2
Keywords
RNA synthesis; activator; 5-(benzylmercapto)-1H-tetrazole
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An improved method for the preparation of 5-(benzylmercapto)-1H-tetrazol as activator in RNA synthesis is described. Reaction of benzylthiocyanate with azide delivers the corresponding tetrazole with 72% yield under optimised conditions. We demonstrate that 5-(benzylmercapto)-1H-tetrazol is a superior activator of 2'-O-TBDMS phosphoramidite building blocks. Compared to routinely used 1H-tetrazol, application of a 0.25 M 5-(benzylmercapto)-1H-tetrazol solution in acetonitrile allows for higher coupling yields (>99%), lower coupling times (3 min) and reduced excess of phosphoramidites in solution over the solid-phase nucleotides (8-fold). (C) 2002 Elsevier Science Ltd. All rights reserved.
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