Literature DB >> 35028893

3,3',5,5'-Tetramethoxybenzoin: a forgotten photolabile protecting group.

Dario Bragagnolo1, Christian G Bochet2.   

Abstract

Although reported several decades ago, 3,3',5,5'-tetramethoxybenzoin esters have not been used as a common photolabile protecting group, contrary to their unsymmetrical 3',5'-dimethoxybenzoin analogues. While the properties of the latter are superior, their tedious synthesis and chemical instability represent a drawback. In this article, we describe a reliable synthetic access to the symmetrical tetramethoxybenzoin derivatives, and show that their photochemical behaviour remain interesting, in particular chromatically orthogonality with respect to nitroveratryl esters.
© 2021. The Author(s), under exclusive licence to European Photochemistry Association, European Society for Photobiology.

Entities:  

Keywords:  Benzoin condensation; Caged compounds; Photochemistry; Protecting groups; Quantum yield

Mesh:

Substances:

Year:  2022        PMID: 35028893     DOI: 10.1007/s43630-021-00150-7

Source DB:  PubMed          Journal:  Photochem Photobiol Sci        ISSN: 1474-905X            Impact factor:   4.328


  7 in total

1.  Orthogonal Photolysis of Protecting Groups Financial support from the Swiss National Science Foundation (grant no.: 21-57044.99) and the Fonds Frédéric Firmenich et Philippe Chuit is gratefully acknowledged.

Authors:  Christian G. Bochet
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

Review 2.  Wavelength-selective cleavage of photoprotecting groups: strategies and applications in dynamic systems.

Authors:  Mickel J Hansen; Willem A Velema; Michael M Lerch; Wiktor Szymanski; Ben L Feringa
Journal:  Chem Soc Rev       Date:  2015-06-07       Impact factor: 54.564

Review 3.  Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.

Authors:  Petr Klán; Tomáš Šolomek; Christian G Bochet; Aurélien Blanc; Richard Givens; Marina Rubina; Vladimir Popik; Alexey Kostikov; Jakob Wirz
Journal:  Chem Rev       Date:  2012-12-21       Impact factor: 60.622

4.  Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.

Authors:  Roy Weinstain; Tomáš Slanina; Dnyaneshwar Kand; Petr Klán
Journal:  Chem Rev       Date:  2020-10-30       Impact factor: 60.622

5.  Studies on a Dithiane-Protected Benzoin Photolabile Safety Catch Linker for Solid-Phase Synthesis.

Authors:  Hong Boon Lee; Shankar Balasubramanian
Journal:  J Org Chem       Date:  1999-05-14       Impact factor: 4.354

6.  Practical synthesis of a dithiane-protected 3',5'-dialkoxybenzoin photolabile safety-catch linker for solid-phase organic synthesis.

Authors:  Montserrat Cano; Mark Ladlow; Shankar Balasubramanian
Journal:  J Org Chem       Date:  2002-01-11       Impact factor: 4.354

7.  Wavelength-controlled orthogonal photolysis of protecting groups.

Authors:  Aurélien Blanc; Christian G Bochet
Journal:  J Org Chem       Date:  2002-08-09       Impact factor: 4.354

  7 in total

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