<i>N</i>-(Trimethylsilyl)imidazole

Grissom, Janet Wisniewski; Gunawardena, G. U.; Gimisis, Thanasis; Cismas, Crina

doi:10.1002/047084289x.rt307.pub2

Encyclopedia of Reagents for Organic Synthesis 2007

DOI: 10.1002/047084289x.rt307.pub2

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N-(Trimethylsilyl)imidazole

Janet Wisniewski Grissom

G. U. Gunawardena

Thanasis Gimisis

et al.

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2021

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“…The major pathway (blue route) begins with the in situ generation of silylimidazole from HSi[OCH(CF 3 ) 2 ] 3 due to the presence of CsF and imidazole as catalysts . Silylimidazoles are among the most powerful protective silyl donors, reacting chemoselectively with alcohols and carboxylic acids in the presence of amines . The resulting silylimidazole undergoes chemoselective silylation with amino acids forming silyl esters A (and/or A′ ).…”

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confidence: 99%

Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents

Muramatsu

Yamamoto

2021

J. Am. Chem. Soc.

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A one-pot peptide bond-forming reaction has been developed using unprotected amino acids and peptides. Two different silylating reagents, HSi[OCH(CF 3 ) 2 ] 3 and MTBSTFA, are instrumental for the successful implementation of this approach, being used for the activation and transient masking of unprotected amino acids and peptides at C-termini and N-termini, respectively. Furthermore, CsF and imidazole are used as catalysts, activating HSi[OCH(CF 3 ) 2 ] 3 and also accelerating chemoselective silylation. This method is versatile as it tolerates side chains that bear a range of functional groups, while providing up to >99% yields of corresponding peptides without any racemization or polymerization.

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confidence: 99%

Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents

Muramatsu

Yamamoto

2021

J. Am. Chem. Soc.

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N-(Trimethylsilyl)imidazole

Cited by 1 publication

References 53 publications

Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents

Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents

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