t-Butylamine as a “new” agent for mild and selective deacetylation
Standing
Undergraduate
Type of Proposal
Oral Presentation
Faculty
Faculty of Science
Faculty Sponsor
Dr. John Trant
Proposal
The selective removal of acetates in the presence of longer chain esters remains a significant challenge in organic chemistry, specifically carbohydrate chemistry. In a recent synthetic project, the Trant group had to remove a series of acetates without cleaving other esters, and all listed chemical methods in Green and Wutz either failed to provide selectivity or degraded the complex carbohydrate. To address this challenge, we had turned to methoxyacetates as an alternative protecting group. Standard conditions for their cleavage involve the use of tert-butylamine, although the precise mechanism of action remains unclear. We happily found that these mild, selective conditions are also appropriate for the acetate group. In this presentation we discuss the potential application of this reagent for the selective hydrolysis of acetates in complex protected carbohydrates, as well our explorations into the chemoselectivity, kinetic profile, and scope and limits of this reaction.
Location
University of Windsor
Grand Challenges
Sustainable Industry
Special Considerations
N/A
t-Butylamine as a “new” agent for mild and selective deacetylation
University of Windsor
The selective removal of acetates in the presence of longer chain esters remains a significant challenge in organic chemistry, specifically carbohydrate chemistry. In a recent synthetic project, the Trant group had to remove a series of acetates without cleaving other esters, and all listed chemical methods in Green and Wutz either failed to provide selectivity or degraded the complex carbohydrate. To address this challenge, we had turned to methoxyacetates as an alternative protecting group. Standard conditions for their cleavage involve the use of tert-butylamine, although the precise mechanism of action remains unclear. We happily found that these mild, selective conditions are also appropriate for the acetate group. In this presentation we discuss the potential application of this reagent for the selective hydrolysis of acetates in complex protected carbohydrates, as well our explorations into the chemoselectivity, kinetic profile, and scope and limits of this reaction.