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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the chemical reagent with formula C 6 Cl 2 (CN) 2 O 2. This oxidant is useful for the dehydrogenation of alcohols, [3] phenols, [4] and steroid ketones. [5] DDQ decomposes in water, but is stable in aqueous mineral acid. [6]
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure. For example, the amino acid tyrosine could be protected as a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert-butyl ether on the phenol
[5] [6] Selective cleavage of the N-Boc group in the presence of other protecting groups is possible when using AlCl 3. Sequential treatment with trimethylsilyl iodide then methanol can also be used for Boc deprotection, [7] [8] especially where other deprotection methods are too harsh for the substrate. [9]
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Deprotection of Boc-protected amines can be achieved using trimethylsilyl trifluoromethanesulfonate and triethylamine or 2,6-lutidine. [ 7 ] [ 8 ] TMSOTf is also a useful reagent to replace metal-halogen bonds with a covalent M-O(SO2CF3) bond, the by-product being the highly volatile TMSCl which is easily removed.
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This might involve using the triflate or the less reactive chloride of TBDPS along with a mild base such as 2,6-lutidine or pyridine and potentially a catalyst such as DMAP or imidazole. [ 3 ] The ease of installation of the protecting group follows the order: 1 o > 2 o > 3 o , allowing the least hindered hydroxyl group to be protected in the ...
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