Selective cleavage of tert-butyl esters in the presence of tert-butyl ethers. Application to the synthesis of tert-butoxy amino acids

We report on the selective cleavage of tert-butyl esters in the presence of tert-butyl ether groups by using trimethylsilyl triflate. The method is especially useful for the synthesis of tert-butyl ethers of N-protected hydroxy amino acids which are valuable building blocks for peptide synthesis.

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 12; pp. 1433 - 1435
Main Authors Trzeciak, A, Bannwarth, W
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.1996
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
trimethylsilyl triflate
deprotection
HYDROLYSIS
TRIMETHYLSILYL IODIDE
QUANTITATIVE DEALKYLATION
tert-butyl ether of hydroxy amino acids
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Summary:We report on the selective cleavage of tert-butyl esters in the presence of tert-butyl ether groups by using trimethylsilyl triflate. The method is especially useful for the synthesis of tert-butyl ethers of N-protected hydroxy amino acids which are valuable building blocks for peptide synthesis.
ISSN:0039-7881
DOI:10.1055/s-1996-4408