Trityl ether
Trityl ethers represent a group of organic chemical compounds that can be viewed as a special case of an ether (R – O – R) in which one of the two organic radicals represents a trityl group .
synthesis
To synthesize trityl ethers, an alcohol is reacted with trityl chloride (Ph 3 CCl, abbreviated as TrCl) in the presence of a base (e.g. pyridine ). For steric reasons, only primary alcohols are etherified with trityl chloride and, in the case of monosaccharides , for example, it is possible to selectively protect the hydroxyl group at C-6 in addition to all others.
meaning
In preparative organic chemistry, the hydroxyl group of alcohols is sometimes protected by introducing a trityl group with the formation of a trityl ether. The trityl ether group is relatively stable to bases but can be split off again relatively easily under acidic conditions, releasing the previously protected hydroxyl group. A para methoxy group on one of the three phenyl groups of the trityl ether promotes the acid lability of the trityl ether. If all three phenyl groups of the trityl ether are methoxy-substituted in the para position, the acid lability of the trityl ether increases. Such protective group strategies are used in nucleotide synthesis.
Individual evidence
- ↑ Jonathan Clayden, Nick Greeves, Stuart Warren, Peter Wothers: Organic Chemistry , Oxford University Press, 2001, p. 1370, ISBN 978-0-19-850346-0 .
- ↑ P. Collins, R. Ferrier: Monosacharides - Their Chemistry and their Roles in Natural Products , Wiley West Sussex 1995, ISBN 0-471-95343-1 .
- ↑ PJ Kocienski: Protecting Groups , 1st edition, Georg Thieme Verlag, Stuttgart 1994, ISBN 3-13-135601-4 .
- ↑ Reinhard Brückner : Reaction Mechanisms , Spectrum Akademischer Verlag, 3rd corrected edition, 2007, pp. 83–85, ISBN 978-3-8274-1579-0 .