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Digitale Medien

Polylithiated β-Peptides: like-Selective C-Terminal Alkylation of Boc-β-HVal-β-HAla-β-HLeu-OMe (1998)

Hintermann, Tobias ; Mathes, Christian ; Seebach, Dieter

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 2379-2387

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Details

ISSN: 1434-193X

Schlagwort(e): β-Peptides ; Polylithiation of peptides ; Li-enolates of peptides ; Back-bone alkylation of β-peptides ; Diastereoselective alkylation of β-peptide enolates ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: A series of N-Boc-protected β-tripeptide derivatives with or without N-methyl groups and with free or Me-ester-protected C terminus has been prepared (8-14, 16, 17). As with α-peptides (→ A), the β-peptide derivatives can be polylithiated (→ B, C). No epimerization of stereogenic centers and no β elimination (exception 17 → 24) is observed upon treatment with bases as strong as tBuLi. The C terminal ester Li-enolate moiety of tetralithio β-tripeptides (cf. C) can be selectively alkylated with methyl, benzyl and allyl halides, and with tert-butyl bromoacetate in yields ranging from 35-80% (8 → 18, 14 → 20-23).

Materialart: Digitale Medien

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