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Der 2‐Trimethylsilyläthyl‐Rest als selektiv abspaltbare Carboxy‐Schutzgruppe
Author(s) -
Sieber Peter
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600822
Subject(s) - chemistry , racemization , fluoride , protecting group , pyridine , trimethylsilyl , peptide , dimethylformamide , ammonium , organic chemistry , medicinal chemistry , peptide synthesis , ammonium fluoride , residue (chemistry) , inorganic chemistry , alkyl , biochemistry , solvent
The 2‐trimethylsilylethyl residue, a selectively cleavable carboxyl protecting group In a search for new carboxyl protecting groups suitable for use in peptide synthesis, 2‐trimethylsilylethyl esters [‐COOCH 2 CH 2 Si(CH 3 ) 3 ] of several N ‐protected amino acids have been prepared. These esters can be synthesized in good yields from N a ‐benzyloxycarbonyl‐amino acids and 2‐trimethylsilylethanol with dicyclohexylcarbodiimide in the presence of pyridine. They are stable under a wide variety of conditions used during coupling and work‐up in peptide synthesis. For removal the 2‐trimethylsilylethyl group is readily cleaved by fluoride ions, preverably using a quaternary ammonium fluoride in dimethylformamide. Some side reactions which occurred during the removal of the 2‐trimethylsilylethyl group are discussed. Special attention has been paid to the question of racemization during the treatment with fluoride ions. No. evidence of racemization was found in any of the cases examined.