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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]
The use of protective groups is pervasive but not without criticism. [103] In practical terms their use adds two steps (protection-deprotection sequence) to a synthesis, either or both of which can dramatically lower chemical yield. Crucially, added complexity impedes the use of synthetic total synthesis in drug discovery.
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R = heteroatom, alkyl, aryl, allyl etc. or other substituents. In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH 2 −C 6 H 5. Benzyl features a benzene ring (C 6 H 6) attached to a methylene group (−CH 2 −). [1]
Trimethylsilyl trifluoromethanesulfonate has a variety of other specialized uses. It has been used to install tert-alkyl groups on phosphine (R = alkyl): [6] PH 3 + R 3 C–OAc + Me 3 SiOTf → [(R 3 C) 2 PH 2]OTf. Deprotection of Boc-protected amines can be achieved using trimethylsilyl trifluoromethanesulfonate and triethylamine or 2,6 ...
The use of triethylsilane as a carbocation scavenger in the presence of trifluoroacetic acid in dichloromethane has been shown to lead to increased yields, decreased reaction times, simple work-up and improved selectivity for the deprotection of t-butyl ester and t-butoxycarbonyl sites in protected amino-acids and peptides in the presence of ...
2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is an organochlorine compound with the formula C 6 H 15 ClOSi, which was developed by Bruce H. Lipshutz during his work on the synthesis of N-methylmaysenine.