Carbocations in Action. Design, Synthesis, and Evaluation of a Highly Acid-Sensitive Naphthalene-Based Backbone Amide Linker for Solid-Phase Synthesis

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• 作者：Michael Pittelkow ; Ulrik Boas ; J//pubs.acs.org/images/gifchars/oslash.gif" border="0">rn B. Christensen
• 刊名：Organic Letters
• 出版年：2006
• 出版时间：December 7, 2006
• 年：2006
• 卷：8
• 期：25
• 页码：5817 - 5820
• 全文大小：197K
• 年卷期：v.8,no.25(December 7, 2006)
• ISSN：1523-7052

文摘

The design, synthesis, and properties of an extremely acid-labile backbone amide linker based on a regiospecifically substituted tetraalkoxynaphthaldehyde core are presented. This handle enables cleavage of peptide backbone amides (secondary amides) off a solid support usingas little as 0.5% TFA in CH₂Cl₂. This proceeds without cleavage of tert-butyl ethers and tert-butyl esters. The design is based on a DFT studythat predicted the most stabile alkoxy-substituted methyl naphthyl carbocation.