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An improved synthesis of adefovir and related analogues.


ABSTRACT: An improved synthesis of the antiviral drug adefovir is presented. Problems associated with current routes to adefovir include capricious yields and a reliance on problematic reagents and solvents, such as magnesium tert-butoxide and DMF, to achieve high conversions to the target. A systematic study within our laboratory led to the identification of an iodide reagent which affords higher yields than previous approaches and allows for reactions to be conducted up to 10 g in scale under milder conditions. The use of a novel tetrabutylammonium salt of adenine facilitates alkylations in solvents other than DMF. Additionally, we have investigated how regioselectivity is affected by the substitution pattern of the nucleobase. Finally, this chemistry was successfully applied to the synthesis of several new adefovir analogues, highlighting the versatility of our approach.

SUBMITTER: Jones DJ 

PROVIDER: S-EPMC6444443 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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An improved synthesis of adefovir and related analogues.

Jones David J DJ   O'Leary Eileen M EM   O'Sullivan Timothy P TP  

Beilstein journal of organic chemistry 20190329


An improved synthesis of the antiviral drug adefovir is presented. Problems associated with current routes to adefovir include capricious yields and a reliance on problematic reagents and solvents, such as magnesium <i>tert</i>-butoxide and DMF, to achieve high conversions to the target. A systematic study within our laboratory led to the identification of an iodide reagent which affords higher yields than previous approaches and allows for reactions to be conducted up to 10 g in scale under mil  ...[more]

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