Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

1129650

Reference Type

Journal Article

Title

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

Author(s)

Plietzsch, O; Schilling, CI; Tolev, M; Nieger, M; Richert, C; Muller, T; Brase, S

Year

2009

Is Peer Reviewed?

Journal

Organic and Biomolecular Chemistry
ISSN: 1477-0520
EISSN: 1477-0539

Volume

Issue

Page Numbers

4734-4743

Language

English

PMID

19865711

DOI

10.1039/b912189g

Web of Science Id

WOS:000271432300023

Abstract

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.