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dM-Dim for carboxylic acid protection
Authors:Shahien Shahsavari  Travis Wigstrom  James Gooding  Chase McNamara  Shiyue Fang
Institution:Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA
Abstract:The 1,3-dithian-2-yl-methyl (Dim) and its analogous groups including dimethyl-Dim (dM-Dim) can provide a new dimension of orthogonality for carboxylic acid protection. They can be deprotected under nearly neutral oxidative conditions. In this paper, the protection of carboxylic acid with dM-Dim, deprotection of dM-Dim ester with sodium periodate, stability of dM-Dim protected carboxylic acid under acidic and basic conditions, and selective deprotection of dM-Dim protected carboxylic acids in the presence of tertiary butyl and methyl esters are presented.
Keywords:Protecting group  Carboxylic acid  Oxidation  dM-Dim
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