46687-57-4

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 63-91-2 L-phenylalanine 
• 3081-24-1 H-Phe-OEt 

Downstream Products

• 3182-95-4 L-Phenylalaninol 
• 123366-90-5 (S)-3-phenyl-2-(1H-pyrrol-1-yl)propan-1-ol 
• 1444003-12-6 (S)-N-(2-formylphenyl)-3-phenyl-2-(1H-pyrrol-1-yl)propanamide 
• 1444003-19-3 (S)-N-(2-acetylphenyl)-3-phenyl-2-(1H-pyrrol-1-yl)propanamide 
• 1444003-10-4 3S,5R,7R,8R,11R-5,8-dihydroxy-5-(4-oxo-3H-quinqzolin-3-yl)-3-benzyl-8-methyl-9,10-benzo-2-oxo-1,4-diazatricyclo[5.3.1.0^4,11]undec-9-ene 
• 1444003-09-1 C₂₄H₂₉N₃O₃ 
• 1444003-06-8 dimethyl (3S,9S,10R,17R)-3-benzyl-10-hydroxy-10-methyl-2-oxo-1,4-diazatetracyclo[7.7.1.0^4,17]heptadeca-5,7,11,13,15-pentaene-6,7-dicarboxylate 
• 1444003-05-7 C₂₇H₂₆N₂O₆ 

Relevant academic research and scientific papers

Catalytic Hydrogenation of N-protected α-Amino Acids Using Ruthenium Complexes with Monodentate Phosphine Ligands

A ruthenium complex with a monodentate phosphine ligand was used to catalytically hydrogenate N-protected α-amino acids under essential retention of the configuration of their α-chiral centers. Among the ligands tested for this hydrogenation, which proceeds at a relatively low temperature, tris(para-fluorophenyl)phosphine exhibited the best performance. In comparison, electron-rich monodentate, bidentate, and tridentate phosphines were far less effective. The precatalyst Ru(OAc)2[(p-FC6H4)3P]2 was synthesized and isolated, and its structure was determined by a single-crystal X-ray diffraction analysis. N-protected α-amino acids with neutral alkyl side chains, including polar functional groups such as sulfides, indoles, ethers, phenols, pyrroles, and arenes, are compatible with the applied hydrogenation conditions, affording the corresponding optically active 2-substituted-2-(1H-pyrrol-1-yl)ethan-1-ol (2-amino ethanol) derivatives in moderate to high yield. (Figure presented.).

Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles

Upon irradiation, cyclic imines containing o-amido groups are shown to produce reactive intermediates, amino azaxylylenes, which undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex N,O-heterocycles having an additional spiro-connected nitrogen heterocyclic moiety. Modular assembly of the photoprecursors allows expeditious increase of the complexity of the target poly-heterocyclic scaffolds with a minimal number of experimentally simple reaction steps. The photocyclization and subsequent postphotochemical transformations are accompanied by an increase of Lovering's fsp3 factor, thus producing unprecedented three-dimensional molecular architectures, and offering extended sampling of chemical space. Rings in three dimensions: Cyclic imines containing an o-amido group undergo excited-state intramolecular proton transfer to generate amino azaxylylenes. The amino azaxylylenes undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex heterocyclic three-dimensional molecular architectures.

Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores

Enantiopure alkaloid mimics are synthesized via high yielding intramolecular cycloadditions of photogenerated azaxylylenes tethered to pyrroles, with further growth of molecular complexity via post-photochemical transformations of primary photoproducts. This expeditious access to structurally unprecedented polyheterocyclic cores is being developed in the context of diversity-oriented synthesis, as the modular design allows for rapid "pre-assembly" of diverse photoprecursors from simple building blocks/diversity inputs.

Friedel-Crafts alkylation of natural amino acid-derived pyrroles with CF3-substituted cyclic imines

Natural amino acid-derived ethyl 2-(1-pyrrolyl)alkanoates react with 2-trifluoromethyl-1-azacycloalkenes selectivity at the β-position of the pyrrole moiety to afford ethyl 2-[3-(1-trifluoromethyl-2-azacycloalkyl)pyrrol-1- yl]alkanoates.

2-(1H-pyrrolyl)carboxylic acids as pigment precursors in garlic greening

Six model compounds having a 2-(1H-pyrrolyl)carboxylic acid moiety and a hydrophobic R group were synthesized to study their effects on garlic greening, the structures of which are similar to that of 2-(3,4-dimethyl-1H-pyrrolyl)-3- methylbutanoic acid (PP

Evaluation of physicochemical parameters important to the oral bioavailability of peptide-like compounds: Implications for the synthesis of renin inhibitors

A series of radiolabeled compounds related to renin inhibitor structures was synthesized to represent a range of physicochemical properties. These compounds were tested in assays for intestinal absorption and hepatic clearance in order to define parameter

Nonpeptide angiotensin II receptor antagonists. 1. Synthesis and in vitro structure-activity relationships of 4[[[(1H-pyrrol-1- ylacetyl)amino]phenyl]methyl]imidazole derivatives as angiotensin II receptor antagonists

A novel series of non-biphenylyltetrazole angiotensin II receptor antagonists which contain a 1H-pyrrol-1-ylacetyl residue in place of the benzoyl residue in EXP 6803 have been developed. The receptor binding activity of several members of this new series

Peptide Synthesis Using the Pyrrole Ring as an Amino Protecting Group

The utility of a pyrrole ring as an amino protecting group for amino acids in peptide synthesis has been studied.The N-termini of various amino acids (1) were protected with a pyrrole ring by treatment with 2,5-dimethoxytetrahydrofuran (10) to give 2-substituted 2-(1-pyrrolyl)acetic acids (11).The peptide bond between (11) and amino acid methyl ester (2) was formed using N,N'-dicyclohexylcarbodiimide, and the pyrrole ring was cleaved by ozonolysis and hydrolysis without the cleavage of a peptide bond to give the corresponding dipeptide compounds (26) in good yields.