Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies

Oliver Plietzsch; Christine Inge Schilling; Mariyan Tolev; Martin Nieger; Clemens Richert; Thierry Muller; Stefan Bräse

doi:10.1039/B912189G

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Organic & Biomolecular Chemistry

Issue 22, 2009

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Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies

Oliver Plietzsch , Christine Inge Schilling , Mariyan Tolev , Martin Nieger , Clemens Richert , Thierry Muller and Stefan Bräse

Org. Biomol. Chem., 2009, 7, 4734-4743

DOI: 10.1039/B912189G
Received 22 Jun 2009, Accepted 04 Aug 2009
First published on the web 14 Sep 2009

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A modular concept for the generation of achiral and chiral non-racemic tetrahedral tectons from common precursors was developed. The tectons presented here are based on tetraphenylmethane or 1,3,5,7-tetraphenyladamantane core structures. They are obtained through high-yielding four-fold click reactions, using either the tetraazido or the tetraalkyne precursors. In most cases, the tetratriazoles are obtained as pure products after simple washing with water and methanol. The side chains of the tectons prepared include a self-complementary DNA dimer, obtained from a 3′-azidonucleoside and a phosphoramidite. The concept allows for a variation of the “sticky ends”, leading to tecton or ligand libraries.

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Oliver Plietzsch
Christine Inge Schilling
Mariyan Tolev
Martin Nieger
Clemens Richert
Thierry Muller
Stefan Bräse

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Organic & Biomolecular Chemistry

Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies

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