Expedient synthesis of a novel asymmetric selectively deprotectable derivative of the ATAC scaffold

Arwin J. Brouwer, Helmus Van De Langemheen, Rob M J Liskamp*

*Corresponding author for this work

    Research output: Contribution to journalArticleAcademicpeer-review

    Abstract

    An efficient multigram scale synthesis of a new asymmetric triazacyclophane scaffold, the ATAC (Asymmetric-TAC) scaffold, bearing three selectively removable groups is described. This scaffold is slightly more rigid than our frequently used TAC (TriAzaCyclophane) scaffold. The synthesis of the required triamine is very high yielding without difficult steps or purifications and was also applied to a much improved synthesis of our original TAC scaffold. Especially the tedious first reaction step, that is, mono-oNBS-protection of a triamine could be omitted. The rigidity of the triazacyclophane ring in both TAC- and ATAC scaffolds has also been investigated using variable temperature 1H NMR experiments.

    Original languageEnglish
    Pages (from-to)4002-4007
    Number of pages6
    JournalTetrahedron
    Volume70
    Issue number26
    DOIs
    Publication statusPublished - 1 Jul 2014

    Keywords

    • Asymmetric scaffold
    • ATAC scaffold
    • Orthogonal protecting groups
    • TAC scaffold
    • Tripodal scaffold

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