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Literature DB >> 33851842

The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation.

Lucrezia De Pascalis, Mei-Kwan Yau, Dennis Svatunek¹, Zhuoting Tan¹, Srinivas Tekkam, K N Houk¹, M G Finn.

Abstract

Oxanorbornadienes (ONDs) undergo facile Michael addition with thiols and then fragment by a retro-Diels-Alder (rDA) reaction, a unique two-step sequence among electrophilic cleavable linkages. The rDA reaction rate was explored as a function of the furan structure, with substituents at the 2- and 5-positions found to be the most influential and the fragmentation rate to be inversely correlated with electron-withdrawing ability. Density functional theory calculations provided an excellent correlation with the experimentally measured OND rDA rates.

Entities: Chemical

Mesh：

Substances：

Year: 2021 PMID： 33851842 PMCID： PMC9020489 DOI： 10.1021/acs.orglett.1c01164

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.072

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The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation.

1. Tracelessness Unmasked: A General Linker Nomenclature.

2. Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry.

Review 3. Activity-based protein profiling: from enzyme chemistry to proteomic chemistry.

Review 4. Cleavable linkers in chemical biology.

5. Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes.

Review 6. Drug delivery and release systems for targeted tumor therapy.

7. Efficient Liver Targeting by Polyvalent Display of a Compact Ligand for the Asialoglycoprotein Receptor.

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