25282-53-5

Upstream product

• 150-30-1 Phenylalanine 
• 100-51-6 benzyl alcohol 
• 47004-38-6 D-phenylalanine benzyl ester 
• 2978-10-1 O-benzyl-N,N'-diisopropylisourea 
• 4530-18-1 2-(tert-butoxycarbonylamino)-3-phenylpropionic acid 
• 100-44-7 benzyl chloride 
• 16367-71-8 t-butyl (RS)-phenylalaninate 
• 501-53-1 benzyl chloroformate 
• 100-52-7 benzaldehyde 
• 6125-24-2 2-Phenylnitroethane 
• 28170-07-2 benzyl phenyl carbonate 
• 302-72-7 rac-Ala-OH 
• 64-19-7 acetic acid 

Downstream Products

• 133075-92-0 N<carbonyl>phenylalanine benzyl ester 
• 146335-67-3 C₂₄H₂₁N₃O₃ 
• 126191-07-9 2-diazo-3-phenylpropanoic acid benzyl ester 
• 63-91-2 L-phenylalanine 
• 962-39-0 L-Phenylalanine benzyl ester 
• 47004-38-6 D-phenylalanine benzyl ester 
• 146335-77-5 3-amino-7-benzyl-1,2,4,6-tetrabicyclo<3.3.0>octan-8-one 
• 146335-86-6 2-(5-Amino-2-methyl-2H-[1,2,4]triazol-3-ylamino)-3-phenyl-propionic acid benzyl ester 
• 146335-88-8 2-(5-Amino-1-methyl-1H-[1,2,4]triazol-3-ylamino)-3-phenyl-propionic acid benzyl ester 
• 131746-55-9 benzyl 2-bromo-2-fluoro-3-phenylpropionate 
• 673-06-3 D-(R)-phenylalanine 
• 1261037-13-1 3-benzyl 1,2-diethyl 3-benzyl-1H-1,2,4-triazole-1,2,3(3H)-tricarboxylate 
• 1261037-14-2 3-benzyl 1,2-di-tert-butyl 3-benzyl-1H-1,2,4-triazole-1,2,3(3H)-tricarboxylate 

Relevant academic research and scientific papers

Bioactive Surfactants containing a &β-Lactam Group: Synthesis and Properties

Selective activation of 3-hydroxy-2-hydroxymethyl-2-methylpropanamide with P(NMe2)3-CCl4, and subsequent intramolecular cyclisation yields β-lactam derivatives that have both surface and antibiotic activity.

O -Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P(O)-NH containing compounds

Over 50 years ago, Jencks and Gilchrist showed that formaldehyde catalyses the hydrolysis of phosphoramidate through electrophilic activation, induced by covalent attachment to its nitrogen atom. Given our interest in the use of aldehydes as catalysts, this work was revisited to identify a superior catalyst, o-phthalaldehyde, which facilitates hydrolyses of various organophosphorus compounds bearing P(O)-NH subunits under mild conditions. Interestingly, chemoselective hydrolysis of the P(O)-N bonds could be accomplished in the presence of P(O)-OR bonds.

A practical aryl unit for azlactone dynamic kinetic resolution: Orthogonally protected products and a ligation-inspired coupling process

The first strategy for bringing about enantioselective azlactone dynamic kinetic resolution to generate orthogonally protected amino acids has been developed. In the presence of a C2-symmetric squaramide-based catalyst, benzyl alcohol reacts with novel yet readily prepared tetrachloroisopropoxycarbonyl-substituted azlactones to generate trapped phthalimide products of significant synthetic interest with excellent enantiocontrol. These materials are masked amino acids which are demonstrably orthogonally protected: cleavage of the phthalimide can be achieved in the presence of the ester and vice versa. This process could be utilized to bring about a highly stereoselective ligation-type coupling of protected serines (at stoichiometric loadings) with racemic azlactones derived from both natural and abiotic amino acids. After deprotection, a subsequent base-mediated Oa??N acyl transfer occurs to form a dipeptide.

Competing benzyl cation transfers in the gas-phase fragmentation of the protonated benzyl phenylalaninates

In this study, the competing benzyl cation transfer reactions have been explored by investigating the gas phase chemistry of the protonated benzyl phenylalaninates. Protonation at the carboxylic O atom results in the breakage of the ester CO bond to afford the benzyl cation, which undergoes the competing migration to the amino N atom or the phenyl ring C atom. Both the amino and the phenyl ring hydrogen atoms can be activated to be mobile due to the electrophilic attack of the transferring benzyl cation, and migration of the activated hydrogen atom to the carboxylic hydroxyl leads to (H2O + CO) elimination of the precursor ion. Interestingly, it is much more preferred for the benzyl cation to transfer to the phenyl ring via the amino N, leading to the stepwise benzyl cation transfer, albeit the amino N atom contains more nucleophilic affinity. The mechanistic processes have been confirmed by the MS3 spectra data, along with D-labeling experiments and theoretical calculations.

Unusual reactivity of nitronates with an aryl alkyl carbonate: Synthesis of α-amino esters

The monoanions of nitroalkanes are ambident nucleophiles that react with carbonate electrophiles through the oxygen atom. Products arising from reactivity at the carbon atom will yield α-nitro esters, which are precursors for α-amino esters. We demonstrate this in the reactions of nitroalkanes with benzyl phenyl carbonate and DABCO where α-nitro esters are obtained instead of nitrile oxides. The products are readily reduced to α-amino esters. This pathway could be a safe alternative to the Strecker reaction.

Concise synthesis of α-methylene-β-hydroxy-γ-carboxy- γ-lactams

A concise protocol for the synthesis of α-methylene-β-hydroxy- γ-carboxy-γ-lactams has been described via alkylation of amino acid derived iminoesters with α-bromomethylmethacrylate, followed by allylic hydroxylation. All the synthesized compounds have been evaluated for their cytotoxicity on multiple myeloma cancer cell lines.

An efficient synthesis of [2.2.1] heterobicyclic pyroglutamates

A novel methodology for the efficient synthesis of [2.2.1] heterobicyclic pyroglutamates has been described. The key synthetic steps involve alkylation of amino acid-derived iminoesters with Baylis-Hillman bromide, RhCl 3-catalyzed exocyclic olefin isomerization, diastereoselective dihydroxylation, and regioselective lactonization. All the compounds were evaluated for their cytotoxicity using multiple myeloma cancer cell lines RPMI 8226.

Enantioselective synthesis of 1,2,4-triazolines by chiral iron(ii)-complex catalyzed cyclization of α-isocyano esters and azodicarboxylates

Enantioselective cyclization of α-isocyano esters with azodicarboxylates catalyzed by FeII-N,N′-dioxide complexes has been developed. Under mild conditions, a variety of 1,2,4-triazoline derivatives was obtained in high yields and enantioselectivities.

PREPARATIONS CONTAINING AMINO ACIDS AND OROTIC ACID

The present invention describes compounds produced from an orotic acid molecule and an amino acid molecule. The compounds being in the form of amino acid orotate compounds bound by an amide linkage and produced by one of two disclosed methods; 1) reacting orotic acid or derivatives thereof with a thionyl halide, and then combining the acyl halide with an amino acid in the presence of dichloromethane and a DMAP catalyst; or 2) protecting the carboxylic acid of an amino acid and then combining the amino acid with a DCC activated orotic acid, followed by removal of the carboxylic acid protecting group. The resulting amino acid orotate amide has an enhanced stability in solution as compared to a related ester. In addition, specific benefits are conferred by the particular amino acid used to form the compounds in addition to, and separate from, the orotate substituent.

Dynamic Kinetic resolution of α-amino acid esters in the presence of aldehydes

A convenient procedure for the racemization of α-amino acid esters in the presence of catalytic amounts of salicylaldehydes is described. The combination of this racemization protocol with lipase-catalyzed ester hydrolysis allows successful dynamic kinetic resolution of various α-amino acid esters. The corresponding α-amino acids are obtained in high yield and optical purity. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.