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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]
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(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.
Chloranil is produced by chlorination of phenol to give hexachlorocyclohexa-2,5-dien-1-one ("hexachlorophenol"). Hydrolysis of the dichloromethylene group in this dienone gives chloranil: [3] C 6 H 5 OH + 6 Cl 2 → C 6 Cl 6 O + 6 HCl C 6 Cl 6 O + H 2 O → C 6 Cl 4 O 2 + 2 HCl. Chloroanil serves as a hydrogen acceptor. It is more electrophilic ...
p-Methoxybenzyl (PMB) is used as a protecting group for alcohols in organic synthesis (4-Methoxybenzylthiol is used to protect thiols). The p -methoxybenzyl group Strong base such as powdered potassium hydroxide or sodium hydride and p -methoxybenzyl halide (chloride or bromide) [ 14 ] [ 15 ]
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.
Completing the cyclooctane ring required 3 more carbon atoms that were supplied by a C2 fragment in an aldol addition and a Grignard C1 fragment (scheme 2).A Mukaiyama aldol addition (magnesium bromide / toluene) took place between aldehyde 7 and ketene silyl acetal 8 with 71% stereoselectivity to alcohol 9 which was protected as the TBS ether 10 (TBSOTf, 2,6-lutidine).
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]