Protection of amines as their tetrachlorophthalimide derivatives, by reaction with the anhydride in the presence of triethylamine, has been found to be useful in oligosaccharide chemistry. The group is stable to a wide range of reagents but can be selectively cleaved with ethylenediamine at lower temperatures than for the parent phthalimide derivatives; in particular, carboxylic esters are not cleaved under these conditions.
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Applications
Protection of amines as their tetrachlorophthalimide derivatives, by reaction with the anhydride in the presence of triethylamine, has been found to be useful in oligosaccharide chemistry. The group is stable to a wide range of reagents but can be selectively cleaved with ethylenediamine at lower temperatures than for the parent phthalimide derivatives; in particular, carboxylic esters are not cleaved under these conditions.
Solubility
Hydrolyzes slowly in water.
Notes
Hygroscopic. Store away from oxidizing agents, acids.
RUO – Research Use Only
Wilfred Howe, A.F.O.M., M.R.C.G.P.; Katherine M. Venables, M.Sc., M.R.C.P.; Michael D. Topping, Ph.D.; Michael B. Dally, M.R.A.C.P.; Rosemarie Hawkins, S.R.N.; J.Stephen Law, M.D.; Anthony J.Newman Taylor, M.Sc., M.R.C.P. Tetrachlorophthalic anhydride asthma: evidence for specific IgE antibody Journal of Allergy and Clinical Immunology. 1983, 71 (1), 5-11.
Gary M. Liss, MD, MS, FRCPC.; David Bernstein, MD.; Leon Genesove, MD, FRCPC.; Jaan O. Roos, MD, FRCPC.; Janet Lim, MD. Assessment of risk factors for IgE-mediated sensitization to tetrachlorophthalic anhydride. Journal of Allergy and Clinical Immunology. 1993, 92 ( 237-247),.
Protection of amines as their tetrachlorophthalimide derivatives, by reaction with the anhydride in the presence of triethylamine, has been found to be useful in oligosaccharide chemistry. The group is stable to a wide range of reagents but can be selectively cleaved with ethylenediamine at lower temperatures than for the parent phthalimide derivatives; in particular, carboxylic esters are not cleaved under these conditions: J. Am. Chem. Soc., 117, 3302 (1995); J. Org. Chem., 61, 432 (1996).