Literature DB >> 12558446

Bis(o-nitrophenyl)ethanediol: A practical photolabile protecting group for ketones and aldehydes.

Aurélien Blanc1, Christian G Bochet.   

Abstract

The ketals of bis(o-nitrophenyl)ethanediol and ketones or aldehydes are smoothly deprotected in neutral conditions by irradiation with 350 nm light. The chemical stability in basic, acidic, and oxidizing media makes this form of protection orthogonal to classical protecting groups. Both racemic and enantiopure forms are readily available in two steps from inexpensive starting materials.

Entities:  

Year:  2003        PMID： 12558446     DOI： 10.1021/jo026347x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  Alcohol, Aldehyde, and Ketone Liberation and Intracellular Cargo Release through Peroxide-Mediated α-Boryl Ether Fragmentation.

Authors:  Ramsey D Hanna; Yuta Naro; Alexander Deiters; Paul E Floreancig
Journal:  J Am Chem Soc       Date:  2016-09-30       Impact factor: 15.419

Review 2.  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

3.  Cascade reactions during coronafacic acid biosynthesis: elongation, cyclization, and functionalization during Cfa7-catalyzed condensation.

Authors:  Eric R Strieter; Alexander Koglin; Zachary D Aron; Christopher T Walsh
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419
  3 in total

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