16367-71-8

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 150-30-1 Phenylalanine 
• 106377-74-6 2-Azido-3-phenyl-propionsaeure-tert-butylester 
• 64923-12-2 tert-butyl N-benzylideneglycinate 
• 100-39-0 benzyl bromide 
• 21685-51-8 D-phenylalanine methyl ester 
• 7622-23-3 L-α-hydroxyhydrocinnamic acid t-butyl ester 
• 128625-57-0 (E)-2-(Benzhydrylidene-amino)-3-phenyl-acrylic acid tert-butyl ester 
• 75898-42-9 (R,S)-tert-butyl 2-bromo-3-phenylpropionate 
• 673-06-3 D-(R)-phenylalanine 
• 621-82-9 Cinnamic acid 
• 102-92-1 cinnamoyl chloride 
• 14990-09-1 tert-butyl cinnamate 
• 113723-87-8 tert-butyl (R)-3'-phenyl-2'-([1R,2E,4R]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylideneamino)propanoate 

Downstream Products

• 61900-41-2 N-Formylphenylalanin-tert-butylester 
• 87136-64-9 Pyoc-Ile-Phe-OtBu 
• 145916-29-6 2-[(S)-2-Amino-3-(2-thiophen-2-yl-thiazol-4-yl)-propionylamino]-3-phenyl-propionic acid tert-butyl ester 
• 150-30-1 Phenylalanine 
• 114155-71-4 tert-butyl 2-(benzylideneamino)-3-phenylpropanoate 
• 2566-22-5 DL-N-benzoylphenylalanine 
• 54582-05-7 N-phenylacetyl-3-phenyl-alanine 
• 110728-29-5 N-phenoxyacetyl-phenylalanine 
• 40279-93-4 2-(Phenylsulphonylamino)-3-phenylpropanoic acid 
• 3588-57-6 Z-DL-Phe-OH 
• 693793-36-1 tert-butyl N-{4-[4-(benzyloxy)phenyl]pyrimidin-2-yl}phenylalaninate 
• 673-06-3 D-(R)-phenylalanine 
• 176371-13-4 tert-butyl (2R)-2-[3-(4-cyanophenyl)-2-oxo-5-oxazolidinylcarbonylamino]-3-phenylpropionate 
• 960149-56-8 ethyl 5-(1-tert-butoxy-1-oxo-3-phenylpropan-2-ylamino)-5-oxopentanoate 

Relevant academic research and scientific papers

Capture-ROMP-release: Application to the synthesis of amines and alkyl hydrazines

Application of a capture-ROMP-release strategy for the chromatography-free purification of Mitsunobu reaction products is described. Norbornenyl-tagged reagents are utilized for standard solution phase Mitsunobu chemistry. Post-reaction phase-switching is accomplished via in situ ring-opening metathesis polymerization (ROMP) followed by precipitation of the polymer with methanol. Release of the product from the polymer affords amines and alkyl hydrazine derivatives with good yields and purities.

Chiral tetraaryl-and tetraalkynylborates as chiral solvating agents for tetraalkylammonium salts

The application of tetracarbon-substituted chiral borate sodium salts (NaBR*4) as NMR chiral solvating agents for various tetraalkylammonium salts (R4NX) has been successfully demonstrated. Ion exchange between R4NX and NaBR*4 proceeded in excellent yields and provided the corresponding dia-stereomeric salts (R4NBR*4). The ee values of the R4NX salts were determined by1H NMR analysis of R4NBR*4. Two types of chiral borates, tetraaryl-and tetraalkynylborates with optically active 1,1′-binaphthyl components were used. At the beginning of this research, we investigated the efficacy of a known chiral tetraar-ylborate developed by Pommerening et al. for R4NX. To expand the possibility of further structural design of the chiral borate, we designed chiral tetraalkynylborates as a new structure. Their synthesis and application are also described.

Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts

Four new phosphorus dendrimeric phase-transfer catalysts are prepared that contain 12 (+)-cinchoninium salts on the surface obtained by the quaternisation of the quinuclidinic N atom. The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O-9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles are used, substituted benzyl bromides give better results than other activated alkyl bromides to afford the corresponding R amino acid derivatives. A comparison of these results with those reported previously for similar cinchoninium salts shows that dendrimers could be a better support than other polymers for this type of organocatalysis.

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.

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.

An efficient asymmetric biomimetic transamination of α-keto esters to chiral α-amino esters

An efficient asymmetric biomimetic transamination of α-keto esters with quinine derivatives as chiral bases was described. A wide variety of α-amino esters containing various functional groups can be synthesized in high yield and enantioselectivity.

MODULATORS OF TLR3/DSRNA COMPLEX AND USES THEREOF

The present invention provides compounds and compositions that can modulate formation of Toll-like receptor 3 (TLR3) and double-stranded RNA (dsRNA) complex, and methods for using the same. In particular, some aspects of the invention provide compounds of the formula (I) compositions comprising and methods for using the same, where n, Ar1, Ar2, X1, X2, X3, Z1, and Z2 are those defined herein.

Heterocycle synthesis via direct C-H/N-H coupling

A method for five- and six-membered heterocycle formation by palladium-catalyzed C-H/N-H coupling is presented. The method employs a picolinamide directing group, PhI(OAc)2 oxidant, and toluene solvent at 80-120 °C. Cyclization is effective for sp2 as well as aliphatic and benzylic sp3 C-H bonds.

Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines

Tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N-N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building b

A practical large-scale synthesis of cyclic RGD pentapeptides suitable for further functionalization through click' chemistry

A multigram batch of the cyclo[Arg-Gly-Asp-d-Phe-Lys] and its N - azido derivative was accomplished via solution-phase synthesis using an epimerization-free fragment condensation. The C-terminus of d-Phe was protected as its tert-butyl ester. Fmoc (Arg, Gly, Asp, d-Phe) and Boc (Lys) groups were used to protect all N - termini. The Ts and NO2 groups, respectively were chosen to protect the guanidine group. The macrocyclization step (between d-Phe and l-Lys) was carried out under TBTU/HOBt or DPPA condensation conditions. Finally, the -amino group of the lysine residue was selectively converted into the azido group by a diazo-transfer reaction. Georg Thieme Verlag Stuttgart New York.