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Synthesis of unique spirocyclic orthoester-type derivatives of isothiazolo[4,3-d]pyrimidine nucleosides.

ABSTRACT: A set of unique nucleoside analogs, containing 'spirocyclic orthoester-type' scaffolds, were synthesized from a common isothiazolo[4,3-d]pyrimidine-riboside precursor. The key reaction, using 1,2-di-heteroatomic nucleophiles (e.g., 1,2-ethandithiol) and BF3•OEt2, converts an exocyclic imine into the spirocyclic analogs. The novel structural scaffold is confirmed through the use of one- and two-dimensional 1H and 13C NMR experiments.

SUBMITTER: Rovira AR

PROVIDER: S-EPMC5785548 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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Synthesis of unique spirocyclic orthoester-type derivatives of isothiazolo[4,3-d]pyrimidine nucleosides.

Rovira Alexander R AR Tor Yitzhak Y

The Journal of antibiotics 20170726 2

A set of unique nucleoside analogs, containing 'spirocyclic orthoester-type' scaffolds, were synthesized from a common isothiazolo[4,3-d]pyrimidine-riboside precursor. The key reaction, using 1,2-di-heteroatomic nucleophiles (e.g., 1,2-ethandithiol) and BF3•OEt2, converts an exocyclic imine into the spirocyclic analogs. The novel structural scaffold is confirmed through the use of one- and two-dimensional 1H and 13C NMR experiments. ...[more]

PMID: 28743975

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