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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]
(1) Fmoc-protected amino group, (2) benzyl ester protected carboxyl group and (3) tert-butyl ether protected phenolic hydroxyl group of Tyrosine. Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure.
Trichloroethyl chloroformate is used in organic synthesis for the introduction of the trichloroethyl chloroformate (Troc) protecting group for amines, thiols and alcohols.It readily cleaves vs other carbamates and can be used in an overall protecting group strategy.
For example, (C 6 H 5)(CH 3) 2 C + is referred to as a "benzylic" carbocation. The benzyl free radical has the formula C 6 H 5 CH 2 •. The benzyl cation or phenylcarbenium ion is the carbocation with formula C 6 H 5 CH + 2; the benzyl anion or phenylmethanide ion is the carbanion with the formula C 6 H 5 CH − 2.
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The o-hydroxyphenacyl PPG has been introduced as an alternative with absorption band shifted closer towards the visible region, however it has slightly lower quantum yields of deprotection (generally 0.1-0.3) due to excited state proton transfer available as an alternative deactivation pathway. [29]
The use of Fmoc as a temporary protecting group for amine at the N-terminus in solid phase synthesis is very widespread for Fmoc/tBu approach, because its removal with piperidine does not disturb the acid-labile linker between the peptide and the resin. [7]
Trimethylsilylacetylene is also used to synthesize diphenylacetylene derivatives in a one-pot Sonogashira coupling, in which the phenylacetylene derivative reacts with a second aryl halide after in-situ deprotection. [3] A less expensive alternative reagent is 2-methylbut-3-yn-2-ol, which after alkynylation is deprotected with base.