"The most important protecting groups for alcohols are ethers and mixed acetals. … Methyl ethers are readily accessible via the Williamson ether synthesis, but harsh conditions are required to deprotect them. … t-Butyl ethers are readily prepared and are stable to nucleophiles, hydrolysis under basic conditions, organometallic reagents, metal hydrides, and mild oxidations. … Benzyl ethers are quite stable under both acidic and basic conditions and toward a wide variety of oxidizing and reducing reagents. Hence, they are frequently used in organic syntheses as protecting groups. … The PMB ether, also referred to as an MPM ether [(4-methoxyphenyl)methyl], is less stable to acids than a benzyl ether. … Trityl ethers have played an important role in the selective protection and manipulation of -CH2OH groups in carbohydrate chemistry. … The popularity of silicon protecting groups stems from the fact that they are readily introduced and removed under mild condition. Moreover, a wide variety of silylating agents are available for tailor-made protection of ROH groups. The THP group is a widely used protecting group; it is readily introduced by reaction of the enol ether dihydropyran with an alcohol in the presence of an acid catalyst. … The use of carboxylic acid esters as protective groups for alcohols is limited since they may undergo acyl substitution, hydrolysis or reduction."
Quote Details
Added by wikiquote-import-bot
Unverified quote
0 likes
Original Language: English
Available Languages (1)
Sources
George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 3 : The Concept of Protecting Functional Groups
https://en.wikiquote.org/wiki/Protecting_group
Revision History
No revisions have been submitted for this quote.
Categories
Protecting group
3 quotes on TrueQuotesView all quotes by Protecting group →
Related Quotes
"The protecting group reagent must react selectively (kinetic chemoselectivity) in good yield to give a protected subs…"
"Protection of the amino group in amino acids plays a crucial role in peptide synthesis. N-Benzyl groups (N-Bn) are es…"
"[M]ost TiO2 has been synthesized from the mineral , FeTiO3 , using the "sulphate" or "chloride" process for nearly 10…"
"There is inadequate evidence in humans for the carcinogenicity of titanium dioxide. ...There is sufficient evidence i…"
"The Working Group considered the body of evidence regarding the pathways and mechanisms by which titanium dioxide and…"
"TiO2 has been classified in humans and animals as biologically inert... and is widely considered to be a "natural" ma…"
"Most titanium dioxide pigment is produced from mineral concentrates by the chloride or sulfate process, either as the…"
"Exposure levels [to titanium dioxide]... are assumed to be low... with the possible exception of workers who handle l…"
"In two studies of rats that inhaled titanium dioxide, one observed an excess incidence of lung tumours... No increase…"
"Titanium dioxide is obtained from a variety of ores that contain [FeTiO3], [TiO2, but may contain up to 10% iron and …"