171406-45-4

Upstream product

• 616-30-8 3-Amino-1,2-propanediol 
• 95065-18-2 Benzoic acid 4-guanidinophenyl ester 
• 98-88-4 benzoyl chloride 
• 57044-25-4 (R)-oxiranemethanol 
• 10283-95-1 N-allylbenzamide 

Downstream Products

• 357276-55-2 (+/-)-3-benzoylamido-1-(4,4'-dimethoxytriphenylmethyl)-2-propanediol 
• 439614-45-6 2-(benzamidomethyl)-1,4,7-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane 
• 439614-46-7 2-(benzamidomethyl)-1,4,7-triazacyclononane 
• 439614-44-5 N-[2,3-bis(p-toluenesulfonyloxy)propyl]benzamide 

Relevant academic research and scientific papers

Lewis Acid-Catalyzed Addition of Benzophenone Imine to Epoxides Enables the Selective Synthesis and Derivatization of Primary 1,2-Amino Alcohols

Benzophenone imine was found to be an effective ammonia surrogate for the selective preparation of primary 1,2-amino alcohols from epoxides, including enantiopure epichlorohydrin, in the presence of catalytic Y(OTf)3. High-throughput screening of 48 Lewis acids quickly identified Y(OTf)3 as an effective mediator of the addition reaction under mild conditions. Following acidic hydrolysis, the primary amino alcohol salt is revealed and partitions into the aqueous solution, while the benzophenone byproduct is easily removed by simple extraction with ethyl acetate. These ammonium salts can be directly Boc-protected or further derivatized without isolation to form benzamides and sulfonamides under Schotten-Baumann-type conditions in up to 79% isolated yield over three steps. This methodology has been used to prepare key intermediates for the synthesis of PRMT5 inhibitors with high enantiopurity as well as numerous other amide and sulfonamide derivatives.

Mechanistically Driven Development of an Iron Catalyst for Selective Syn-Dihydroxylation of Alkenes with Aqueous Hydrogen Peroxide

Product release is the rate-determining step in the arene syn-dihydroxylation reaction taking place at Rieske oxygenase enzymes and is regarded as a difficult problem to be resolved in the design of iron catalysts for olefin syn-dihydroxylation with potential utility in organic synthesis. Toward this end, in this work a novel catalyst bearing a sterically encumbered tetradentate ligand based in the tpa (tpa = tris(2-methylpyridyl)amine) scaffold, [FeII(CF3SO3)2(5-tips3tpa)], 1 has been designed. The steric demand of the ligand was envisioned as a key element to support a high catalytic activity by isolating the metal center, preventing bimolecular decomposition paths and facilitating product release. In synergistic combination with a Lewis acid that helps sequestering the product, 1 provides good to excellent yields of diol products (up to 97% isolated yield), in short reaction times under mild experimental conditions using a slight excess (1.5 equiv) of aqueous hydrogen peroxide, from the oxidation of a broad range of olefins. Predictable site selective syn-dihydroxylation of diolefins is shown. The encumbered nature of the ligand also provides a unique tool that has been used in combination with isotopic analysis to define the nature of the active species and the mechanism of activation of H2O2. Furthermore, 1 is shown to be a competent synthetic tool for preparing O-labeled diols using water as oxygen source.

Synthesis of phosphonoglycine backbone units for the development of phosphono peptide nucleic acids

A series of phosphono-modified backbone mimics based on achiral and chiral N-(dihydroxypropyl)glycine units were obtained by sequential addition of phosphonate and nucleobase moieties to suitably protected dihydroxypropylamines. Simple synthetic strategies enabled the preparation of various target derivatives that will be useful as building blocks for the preparation of new synthetic polymers containing a phosphonate internucleotide linkage in place of the standard phosphodiester bond. Copyright

5′-substituted-6-carboxylic-2,2′-bipyridine acid: A pivotal architecton for building preorganized ligands

A set of ligands bearing 6-bromo-2,2′-bipyridine pendant arms attached in the 5′-position are described. Transformation of the bromo to an ester was performed by a carboethoxylation reaction promoted by low-valent Pd(0), while saponification followed by acidification gave the acids. The introduction of an appended function 3-nitrobenzyl, benzamidomethyl, and tert-butylacetyl opens the way to further functionalize these scaffolds for potential labeling of biological material. The synthetic protocols represent a valuable approach to the rational design of ligands bearing oxophilic and anionic sidearms.

N-acylation reactions performed in aqueous reaction medium: Screening and optimising of a synthetic step of a process for iodixanol

This contribution presents results from a development and optimisation project concerning a synthetic process for iodixanol. Iodixanol is the "active ingredient" in Visipaque (Nycomed Amersham now Amersham Health) a medical X-ray imaging contrast agent. T

Amide group assisted 3′-dephosphorylation of oligonucleotides synthesized on universal A-supports

(±)-3-Amino-1-(4,4′-dimethoxytriphenylmethyl)-2-propanediol was attached to succinylated alkylamino-controlled pore glass via the second amide bond. The resulting solid phase was acylated to give seven new universal solid supports, compatible with the preparation of all common types of oligodeoxyribonucleotides. These resins allow for fast elimination of the 3′-terminal phosphodiester or phosphorothioate function by ammonia in methanol at room temperature.

Protease catalysis mediated by a substrate mimetic: A novel enzymatic approach to the synthesis of carboxylic acid amides

We present a protease-based method for the coupling of non-coded and non-amino-acid-derived amines with carboxy components. The key feature of this approach is the combination of the substrate-mimetic strategy with the ability of the cysteine protease clostripain to accept a wide spectrum of amines. Firstly, we tested the use of the 4-guanidinophenyl ester leaving group to mediate acceptance of non-coded and non-amino-acid-derived acyl residues. This employed β-amino acid and simple carboxylic acid moieties as acyl donors, and several amino acid and peptide units as acyl acceptors. The study was completed by the use of non-amino-acid-derived acyl acceptors comprising simple amines, amino alcohols, and diamines. The results indicate that the approach presented is a useful strategy for the synthesis of peptide isosteres, peptide analogues, and organic amides. These last open a new range of synthetic applications of proteases completely beyond peptide synthesis, achieving efficient and selective acylations of non-amino-acid-derived amines under extraordinarily mild reaction conditions.

Phosphate linked oligomers

Novel ethylene glycol compounds bearing various functional groups are used to prepare oligomeric structures. The ethylene glycol monomers can be joined via standard phosphate linkages including phosphorothioate, phosphodiester, and phosphoramidate linkages. Useful functional groups include nucleobases as well as polar groups, hydrophobic groups, ionic groups, aromatic groups and/or groups that participate in hydrogen-bonding.