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Synthesis of DDQ involves cyanation of chloranil. J. Thiele and F. Günther first reported a 6-step preparation in 1906. [7] The substance did not receive interest until its potential as a dehydrogenation agent was discovered. A single-step chlorination from 2,3-dicyanohydroquinone was reported in 1965. [8]
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.
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 ]
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[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]
Desulfonylation reactions are chemical reactions leading to the removal of a sulfonyl group from organic compounds.As the sulfonyl functional group is electron-withdrawing, [1] methods for cleaving the sulfur–carbon bonds of sulfones are typically reductive in nature.
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 ...
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