439694-28-7

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 63-91-2 L-phenylalanine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 111525-66-7 (3(2S),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone 
• 501-52-0 3-Phenylpropionic acid 
• 136159-65-4 (S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one 

Downstream Products

• 923293-47-4 (3S,6S)-1-allyl-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]piperazine-2,5-dione 
• 1160187-26-7 (S)-(2-azdio-3-(but-2-ynyloxy)propyl)benzene 
• 1160187-24-5 (S)-(2-azido-3-(prop-2-ynyloxy)propyl)benzene 
• 1260955-40-5 (S)-2-azido-1-benzyloxy-3-phenylpropane 
• 1260955-46-1 1-(S)-((1-hydroxymethyl-2-phenyl)ethyl)-4-phenyl-1H,1,2,3-triazole 
• 1260955-44-9 1-((S)-(1-hydroxymethyl-2-phenyl)ethyl)-1H-1,2,3-triazole-4-carboxylic acid methyl ester 
• 1313531-36-0 C₂₀H₂₆N₄O₃ 
• 1313531-18-8 C₁₇H₂₀N₄O₃ 
• 1313531-37-1 C₂₃H₂₄N₄O₃ 
• 1313531-35-9 C₂₀H₂₈N₄O₃Si 
• 1313531-38-2 C₂₃H₂₃N₅O₅ 
• 1313531-16-6 C₁₄H₂₀N₄O₂ 
• 1380230-90-9 (S)-2,5-dioxopyrrolidin-1-yl (2-azido-3-phenylpropyl)carbamate 
• 1380230-82-9 C₉H₁₂N₄ 

Relevant academic research and scientific papers

Conformations and receptor activity of desmopressin analogues, which contain γ-turn mimetics or a ψ[CH2O] isostere

Three analogues of the antidiuretic drug desmopressin ([1-desamino,8-D-arginine]vasopressin) have been prepared. In two of these, γ-turn mimetics based on a morpholin-3-one framework have been inserted instead of residues Phe3-Asn5, whereas the third anal

Palladium(II), silver(I), and gold(I) complexes of a new class of chiral bicyclic [1,2,3]-triazolooxazine derived N-heterocyclic carbenes (NHCs): Synthesis, structure and application studies

A new class of chiral bicyclic [1,2,3]-triazolooxazine derived N-heterocyclic carbene (NHC) ligands was synthesised in its enantiopure form from commercially available, cheap amino acid without undertaking any chiral resolution. In particular, the bicycli

A concise enantioselective synthesis of (R)-selegiline, (S)-benzphetamine and formal synthesis of (R)-sitagliptin via electrophilic azidation of chiral imide enolates

A concise and high yielding enantioselective synthesis of (R)-selegiline, an anti-Parkinson's drug, (S)-benzphetamine, an anti-obesity agent, and (S)-sitagliptin, an anti-diabetic drug has been described starting from commercially available starting materials employing Evans' electrophilic azidation of chiral imide enolates as a key chiral inducing step, which proceeds in a highly diastereoselective manner (>99%).

Microwave-enhanced solid-phase synthesis of N,N′-linked aliphatic oligoureas and related hybrids

A practical and efficient microwave-assisted solid-phase method for the synthesis of N,N′-linked oligoureas and related amide/urea hybrid oligomers, featuring the use of succinimidyl (2-azido-2-substituted ethyl) carbamate monomers, is reported. The rate enhancement of urea formation under microwave irradiation combined with the mild conditions of the phosphine-based azide reduction makes this approach very effective for routine synthesis of oligoureas and possibly for library production.

Design, synthesis and evaluation of triazole functionalized ring-fused 2-pyridones as antibacterial agents

Antibacterial resistance is today a worldwide problem and the demand for new classes of antibacterial agents with new mode of action is enormous. In the strive for new antibacterial agents that inhibit pilus assembly, an important virulence factor, routes to introduce triazoles in position 8 and 2 of ring-fused bicyclic 2-pyridones have been developed. This was made via Sonogashira couplings followed by Huisgen 1,3-dipolar cycloadditions. The method development made it possible to introduce a diverse series of substituted triazoles and their antibacterial properties were tested in a whole cell pili-dependent biofilm assay. Most of the twenty four candidates tested showed low to no activity but interestingly three compounds, one 8-substituted and two 2-substituted, showed promising activities with EC50's between 9 and 50 μM.

Click chemistry inspired synthesis of ferrocene amino acids and other derivatives

This work reports the synthesis of a wide range of ferrocenyl-amino acids and other derivatives in excellent yield. Diverse amino acid containing azides were synthesized and ligated to ferrocene employing click reaction to access ferrocenyl amino acids. Chiral alcohols, esters, diols, amines containing azido group were tagged to ferrocene via click reaction to generate ferrocene derived chiral derivatives. A novel strategy for direct incorporation of ferrocene into a peptide and a new route to 1, 1′disubstituted ferrocene amino acid derivative are reported.

Intramolecular azide-alkyne [3 + 2] cycloaddition: Versatile route to new heterocyclic structural scaffolds

Investigating the relatively unexplored intramolecular version of the azide-alkyne [3 + 2] cycloaddition, the present studies demonstrate the utility of the above reaction in the synthesis of a variety of as yet unreported heterocyclic structural scaffolds. The approach involved initial installation of strategic azide and alkyne moieties on a common structural framework, followed by their intramolecular cycloaddition studies. The pivotal azidoalkyne intermediates were efficiently accessed from a variety of easily available starting materials such as olefins, epoxides, amino acids, amino alcohols, ketones etc. The key reactions for incorporation of the azide functionality into the desired framework involved azidolysis of epoxides, displacement of hydroxy groups with azide nucleophiles, and diazo transfer on amine. Attachment of the desired alkyne functionalities was accomplished by either N-, or, O-alkylation with appropriate propargylic halides. The azidoalkynes thus prepared underwent smooth intramolecular cycloaddition, resulting in a variety of novel triazolooxazine and triazolopyrazine derivatives. Interestingly, unlike in the intermolecular version, metal catalysis was not necessary for the performance of the above cycloadditions. It is expected that the results from the present studies and its further extension will provide a potentially fertile pathway to a variety of unique chemical entities of structural and biological significance.

Synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives from amino acids

A versatile method for the synthesis of chiral 1,4-disubstituted-1,2,3- triazole derivatives starting from easily accessible naturally occurring D-or L-amino acids as chiral synthons is described. The amino acids were converted into azido alcohols, followed by copper catalyzed [3+2] cycloaddition reactions between the azido alcohols and methyl propiolate and subsequent ester aminolysis with primary and secondary amines furnished the target compounds, which were obtained in excellent yields with no racemization. Docking of selected target compounds shows that the chiral 1,4-disubstituted-1,2,3-triazoles derivatives has the potential of mimicking the binding mode of known purine analogues.

Optically active (peptido-carbene)palladium complexes: Towards true solid-phase combinatorial libraries of transition metal catalysts

This work explores the potential of forming transition metal catalysts by combinatorial solid-phase peptide chemistry to produce catalysts with enzyme-like properties of stereoselectivity, regioselectivity and even substrate selectivity. A series of new functionalised carbene precursors/donors - imidazolium salts - each containing both amino acid and carboxylic acid functionality was synthesised in solution. The readily accessible carbene precursors were incorporated within the backbones of peptides attached to PEGA resin, by standard solid-phase peptide coupling techniques. The synthetic strategy gave easy access to both mono- and didentate ligand systems, providing folded structures around the central transition metal atoms, with different degrees of steric congestion and bite angles. Changing the number of incorporated amino acids between the two carbene donors facilitated variation of the properties of the complexes. Both ligand systems were complexed to palladium(II) by standard base treatment, and the Pd complexes were studied by mass spectrometry and NMR spectroscopy. The monodentate (carbene) palladium complexes were each the product of enolisation of a neighbouring carbonyl group and loss of a proton, followed by coordination of the oxy anion to the palladium atom. The established methods are suitable for the combinatorial synthesis of palladium catalysts on solid support. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Modular synthesis of cyclic peptidomimetics inspired by γ-turns

(Chemical Equation Presented) A series of peptidomimetics based on a γ-turn motif were synthesized using a modular approach, in which N-protected piperidones were reacted with a selection of 2-hydroxyalkyl azides derived from common L-amino acids. Hydrolysis of the initially formed iminium ethers afforded the targeted series of substituted 1,4-diazepin-5-ones.