Trityl group

Structure of the trityl group

The trityl group (trityl comes trityl group) is one of the univalent substituents in the organic chemistry, and I am referred -C(C₆H₅)₃. It is triphenyl methyl radical. I am used as a protecting group to hydroxy groups and am abbreviated to Tr or Trt on the structural formula.

Table of contents

Property

Because trityl cation (C₆H₅₎3^C+ (Tr⁺) is stabilized by the conjugate with three phenyl groups, I do, for example, trityl ether R-O-Tr as follows and am cleaved with acid easily.

R-O-Tr + H⁺ → R-OH + Tr⁺

Using this property, I am used as the protecting group which I can deprotect by acid. On the other hand, the trityl protection is relatively durable for a base and a reducing agent, an oxidizer, a nucleophilic reagent. I receive deprotection like benzylic for the bare resolution to add water to.

Use

Protection

When trityl protects a hydroxy group, I usually perform it by trityl chloride and the Williamson ether synthesis using the organic base (DMAP, corydine, DBU).

R-OH + Tr-Cl + DMAP → R-O-Tr

Fluoroboric acid 1 - trityl pyridinium (Tr-NC₅H₅⁺ tetraas a stronger tritylation agent•BF₄^-) and trimethylsilyl trityl ether (I use it with Tr-O-Si(CH₃)₃, acid) are known. Carboxylic acid and thiol, amine, amide can protect trityl if I choose the condition.

Deprotection

When I exclude the trityl basis, I usually use Bronn's Ted acid and Lewis acids such as the trifluoro acetic acid. The deprotection by the bare resolution to add water to is performed.

Relative

The substituted triphenyl methyl radical which kept a functional group on the phenyl group of the trityl group is also used as a protecting group. Because deprotection with the acid is easier than a trityl group, p-methoxyphenyl diphenyl methyl radical (MMTr) and di(p-methoxyphenyl) phenyl methyl radical (DMTr) are used for nucleosidic 5'-OH protection.

References

• Wuts, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis, 5th ed., WILEY, 2007.

Allied item

• Triphenylmethane
• Benzylic

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