Redox N-Alkylation of Tosyl Protected Amino Acid and Peptide Esters.
نویسندگان
چکیده
منابع مشابه
One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters
An improved protocol for the synthesis of enantiomerically pure allylic amines is reported. N-Protected α-amino esters derived from natural amino acids were submitted to a one-pot tandem reduction-olefination process. The sequential reduction with DIBAL-H at -78 °C and subsequent in situ addition of organophosphorus reagents yielded the corresponding allylic amines without the need to isolate t...
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Solid-phase peptide synthesis in the N-to-C direction, opposite to the classical C-to-N direction of peptide synthesis, provides the synthetically versatile C-terminal carboxyl group for further modification into C-terminally modified peptide mimetics. These are of general interest as potential bioactive agents, particularly as protease inhibitors. Elaboration of peptide mimetics on the solid-p...
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cardiovascular system, namely ANP (atrial natriuretic peptide) and ACE (angiotensin-converting enzyme) has suggested that a dual inhibitor against both enzymes might be a promising drug for the treatment of hypertension and congestive heart failure. Based on this concept, extensive efforts to find a potent and well-balanced compound have been published. Researchers in our Drug Discovery Divisio...
متن کاملConcise and diastereoselective approach to syn- and anti-N-tosyl-a-hydroxy b-amino acid derivatives
The methyl diazoacetate and aryl (N-tosyl)imines can be transformed into syn or anti a-hydroxy b-amino esters with high diastereoselectivities in three steps: the base promoted nucleophilic condensation of the methyl diazoacetate and aryl (N-tosyl)imines to give b-(N-tosyl)amino a-diazoesters, followed by oxidation with Oxone to generate a-oxo esters, which were reduced with NaBH4 to yield the ...
متن کاملTin(II) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement.
A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
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ژورنال
عنوان ژورنال: Acta Chemica Scandinavica
سال: 1994
ISSN: 0904-213X
DOI: 10.3891/acta.chem.scand.48-0324