184176-05-4

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 766-85-8 3-methoxy-1-iodobenzene 
• 900800-02-4 2S-tert-butoxycarbonylamino-3-(3-hydroxyphenyl)propionic acid methyl ester 
• 587-33-7 m-tyrosine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 55477-80-0 methyl 2-[(tert-butoxycarbonyl)amino]acrylate 
• 74-88-4 methyl iodide 
• 261360-71-8 N-tert-butoxycarbonyl-3-methoxy-L-phenylalanine 

Downstream Products

• 1300035-21-5 methyl (S)-3-(2-bromo-5-methoxyphenyl)2-((tert-butyloxycarbonyl)amino)propanoate 
• 1300035-24-8 tert-butyl (S)-(3-(2-bromo-5-methoxyphenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate 
• 1300035-25-9 tert-butyl (S)-(3-(2-bromo-5-methoxyphenyl)-1-(3-methoxyphenyl)-1-oxopropan-2-yl)carbamate 
• 672965-18-3 (R)-N-(2,6-dimethylbenzyl)-3-[(2S,3S)-3-amino-2-hydroxy-4-(3-methoxyphenyl)butanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 672965-08-1 (R)-N-(2-methylbenzyl)-3-[(2S,3S)-3-amino-2-hydroxy-4-(3-methoxyphenyl)butanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 672965-06-9 Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-(3-methoxy-phenyl)-1-methylsulfanylcarbonyl-propyl ester 
• 672965-04-7 acetic acid 3-tert-butoxycarbonylamino-4-(3-methoxy-phenyl)-1-methylsulfanyl-2-oxo-butyl ester 
• 672965-07-0 (2S,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-(3-methoxyphenyl)butyric acid 
• 672965-03-6 [3-methanesulfinyl-1-(3-methoxy-benzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Enhanced copper-mediated 18F-fluorination of aryl boronic esters provides eight radiotracers for PET applications

[18F]FMTEB, [18F]FPEB, [18F]flumazenil, [18F]DAA1106, [18F]MFBG, [18F]FDOPA, [18F]FMT and [18F]FDA are prepared from the corresponding arylboronic esters and [18

Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: Formal synthesis of (-)-haouamine A

A tandem Prins/Friedel-Crafts reaction useful for the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids and a formal synthesis of (-)-haouamine A are described.

Evidence for the role of tetramethylethylenediamine in aqueous negishi cross-coupling: Synthesis of nonproteinogenic phenylalanine derivatives on water

The structure of the alkylzinc-tetramethylethylenediamine (TMEDA) cluster cation 3 has been determined in the gas phase by a combination of tandem mass spectrometry, infrared multiphoton dissociation (IRMPD) spectroscopy, and DFT calculations. Both sets of experimental results establish the existence of a strongly stabilizing interaction of TMEDA with the zinc cation. High-level DFT calculations on the alkylzinc-TMEDA cluster cation 3 allowed the identification of two low energy conformers, each featuring a four-coordinate zinc atom with a bidentate TMEDA ligand, and internal coordination from the carbonyl group of the Boc group to zinc. The experimental IRMPD spectrum is reproduced with an appropriately weighted combination of the IR spectra of the two conformers identified by theory. DFT calculations on the structure of the alkylzinc halide 2 with coordinated TMEDA using the PCM model of water solvent suggest that TMEDA can promote ionization of the zinc-iodine bond in organozinc iodides under aqueous conditions, providing a credible explanation for the role of TMEDA in stabilizing the carbon-zinc bond. Reaction of the serine-derived iodide 1 with aryl iodides "on water", promoted by nano zinc in the presence of PdCl2 (Amphos) 2 (5 mol %) and TMEDA, leads to the formation of protected phenylalanine derivatives 4 in reasonable yields. In the case of ortho-substituted aryl iodides and aryl iodides that are solids at room temperature, conducting the reaction at 65°C gives improved results. In all cases, the product 5 of reductive dimerization of the iodide 1 is also isolated.

Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides

(Chemical Equation Presented) A combination of Pd2(dba) 3 and SPhos (1:2 molar ratio) is an excellent precatalyst for the Negishi cross-coupling of the serine-derived organozinc reagent 2 with aryl halides, including previously difficult ortho-substituted examples. In the case of meta- and para-substituted aryl halides, Pd-loadings of 0.5 mol % give satisfactory results. Use of 2-iodoaniline as substrate gives the lactam 12 in good yield. 2009 American Chemical Society.

Access to enantioenriched α-amino esters via rhodium-catalyzed 1,4-addition/enantioselective protonation

Conjugate addition of potassium trifluoro(organo)borates 2 to dehydroalanine derivatives 1, mediated by a chiral rhodium catalyst and in situ enantioselective protonation, afforded straightforward access to a variety of protected α-amino esters 3 with high yields and enantiomeric excesses up to 95%. Among the tested chiral ligands and proton sources, Binap, in combination with guaiacol (2-methoxyphenol), an inexpensive and nontoxic phenol, afforded the highest asymmetric inductions. Organostannanes have also shown to participate in this reaction. By a fine-tuning of the ester moiety, and using Difluorophos as chiral ligand, increased levels of enantioselectivity, generally close to 95%, were achieved. Deuterium labeling experiments revealed, and DFT calculation supported, an unusual mechanism involving a hydride transfer from the amido substituent to the α carbon explaining the high levels of enantioselectivity attained in controlling this α chiral center.

Negishi cross-coupling reactions of α-amino acid-derived organozinc reagents and aromatic bromides

The Negishi cross-coupling reaction of organozinc iodides derived from α-amino acids with aromatic bromides to give substituted phenylalanine derivatives is described, using either Pd(OAc)2 or Pd2(dba)3 in combination with P(o-Tol)3 as catalyst in DMF at 50 °C. Similar results are obtained using Pd[PtBu3]2 as catalyst. The difference in reactivity displayed between aryl iodides and bromides (ArI>ArBr) has been utilised in a short synthesis of an unsymmetrical, orthogonally protected para-phenylene bis-alanine derivative.

Structure-activity and structure-metabolism relationships of HIV protease inhibitors containing the 3-hydroxy-2-methylbenzoyl-allophenylnorstatine structure

A series of peptidomimetic human immunodeficiency virus (HIV) protease inhibitors containing substituted allophenylnorstatine [Apns: (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid] were designed and synthesized. From the structure-metabolism relationship of this type of HIV protease inhibitors, the compounds having para substitution of the phenyl ring of Apns and/or 2,6-disubstitution of the P2′ benzylamine were found to be able to avoid the P2 phenol glucuronidation that occurs with SM-319777 (formerly named JE-2147, KNI-764); one of the main metabolic pathways of SM-319777. These new analogues, such as SM-322377, had more desirable pharmacokinetic profiles and more potent antiviral activity against not only wild type HIV-1 but also the multi-drug-resistant HIV-1 than SM-319777.