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The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di- tert -butyl dicarbonate in the presence of a base such as sodium hydroxide :
Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. [1]Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride.
tert-Butyloxycarbonyl (Boc) group — Removed by concentrated strong acid (such as HCl [52] or CF 3 COOH [53]), or by heating to >80 °C. Common in solid phase peptide synthesis . 9-Fluorenylmethyloxycarbonyl ( Fmoc ) group — Removed by base, such as 20–50 % piperidine in dimethylformamide (DMF) [ 54 ] or N -Methyl-2-pyrrolidone , [ 55 ] or ...
tert-Butoxycarbonyl, abbreviated as "Boc", "BOC" or "t-Boc", a protecting group used in organic chemistry; Banks: Bank of Canada, Canada's central bank; Bank of Ceylon, a major government-owned commercial bank in Sri Lanka; Bank of China, a major state-owned bank in the People's Republic of China; Bank of Cyprus, a major Cypriot financial ...
The use of the Bergmann-Zervas method remained the standard practice in peptide chemistry for two full decades after its publication, superseded by newer methods (such as the Boc protecting group) in the early 1950s. [34] Nowadays, while it has been used periodically for α-amine protection, it is much more commonly used for side chain protection.
Fmoc-carbamate is frequently used as a protecting group for primary and secondary amines, where the Fmoc group can be introduced by reacting the amine with fluorenylmethyloxycarbonyl chloride (Fmoc-Cl), e.g.: [3]
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.
Benzyl chloroformate is commonly used in organic synthesis for the introduction of the benzyloxycarbonyl (formerly called carboxybenzyl) protecting group for amines.The protecting group is abbreviated Cbz or Z (in honor of discoverer Zervas), hence the alternative shorthand designation for benzyl chloroformate as Cbz-Cl or Z-Cl.