Related Experiment Video
Updated: Aug 19, 2026

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
Published on: September 5, 2018
DMOBO: an improvement on the OBO orthoester protecting group
1Department of Chemistry, SUNY-ESF, Syracuse, NY 13210, USA. jlginer@syr.edu
Abstract:
[reaction: see text] Conversion of a carboxylic acid to an orthoester provides protection toward nucleophiles and strong bases. The addition of methyl substituents to the oxetane precursor of the commonly used [2.2.2]-bicyclic OBO orthoester significantly increased the ease of orthoester formation and its resistance to hydrolysis. NMR kinetics show the DMOBO protecting group is formed 85 times faster than the OBO group, and that its stability toward aqueous hydrolysis is 36 times greater. Nucleophilic attack of the ester carbonyl on the oxetane ring was shown by 18O-labeling to take place at the most substituted position.
More Related Videos
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
05:48Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
Published on: November 21, 2017
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Directing Effect of Substituents: ortho–para-Directing Groups
Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Protecting Groups for Aldehydes and Ketones: Introduction
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Diazonium Group Substitution: –OH and –H