7535-56-0

Usage

Uses

Used in Pharmaceutical Industry:
BOC-PHE-ONP is used as a coupling reagent for the synthesis of peptide-based drugs and therapeutics. Its protective and leaving groups facilitate selective deprotection and the formation of peptide bonds, enhancing the efficiency and specificity of peptide synthesis processes.
Used in Solid-Phase Peptide Synthesis:
In solid-phase peptide synthesis, BOC-PHE-ONP is used as a key component to enable the stepwise assembly of peptide chains. The BOC group protects the amine during synthesis, while the ortho-nitrophenyl group allows for easy displacement in nucleophilic substitution reactions, promoting the formation of peptide bonds and the successful synthesis of desired peptide sequences.

InChI:InChI=1/C20H22N2O6/c1-20(2,3)28-19(24)21-17(13-14-7-5-4-6-8-14)18(23)27-16-11-9-15(10-12-16)22(25)26/h4-12,17H,13H2,1-3H3,(H,21,24)

Upstream product

• 16214-37-2 N-Carbonyl-phenylalanin- 
• 75-65-0 tert-butyl alcohol 
• 100-02-7 4-nitro-phenol 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 107960-06-5 1,2,2,2-tetrachloroethyl 4-nitrophenyl carbonate 
• 13303-10-1 tert-Butyl 4-nitrophenyl carbonate 
• 16480-57-2 L-phenylalanine sodium salt 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 78452-02-5 tert-butyl (S)-1-((S)-1-hydroxy-4-methylpentan-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 
• 94236-51-8 Boc-L-Phe-L-Asp(Bzl)-NH₂ 
• 131697-26-2 Boc-Phe-Leu-Pro-Glu(OBzl)-Gly-OMe 
• 89343-13-5 BOC-Phe-D-Trp-Lys(MSC)-Thr-Phe-Cys(ACM)-OPSE 
• 78731-97-2 BOC-Phe-D-Trp-Lys(MSC)-Thr-Phe-Thr-Ser-Cys(ACM)-OPSE 
• 79432-59-0 Boc-Phe-Glu(OBu^t)-Glu(OBu^t)-Ala-Tyr-Ile-Pro-OBu^t 
• 89343-42-0 BOC-Phe-D-Trp-Lys(MSC)-Thr-Phe-Phe-D-Cys(ACM)-OPSE 
• 119866-67-0 (S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-4-methyl-pentanoic acid 2-cyano-ethyl ester 
• 83704-76-1 Boc-Phe-Ala-NHNHZ 
• 87163-42-6 BOC-Phe-Ser-Tyr-D-Ala-Leu-Arg-Pro-NHEt 
• 17663-35-3 L-phenylalanine p-nitrophenyl ester 
• 23420-32-8 N-tert-butoxycarbonyl-L-phenylalanyl-L-proline 
• 196192-19-5 Boc-Phe-His(Bom)-OOde 
• 196192-20-8 Boc-Phe-His(Dnp)-OOde 

Relevant academic research and scientific papers

Synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane

The invention relates to the technical field of synthesis of drug intermediates, in particular to a synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane. The method comprises the following steps: condensing N-t-butyloxycarboryl-L-phenylalanine serving as a raw material with substituted phenol under the action of a condensing agent to obtain active ester 15; reacting the active ester 15 with a ylide reagent and alkali to obtain a sulfoxide ylide intermediate 16; reacting the sulfoxide ylide intermediate 16 with halide salt under the action of a catalyst to obtain a halogenated ketone intermediate 6; reducing the halogenated ketone intermediate 6 through a reducing agent under the action of a catalyst to obtain a halogenated methanol intermediate 7; and removing halogen acid from the halogenated methanol intermediate 7 under the action of alkali, and carrying out condensation cyclization to obtain the target product (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane. The synthesis method of the (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane, provided by the invention, has the characteristics of cheap and easily available initial raw materials, safe and controllable process and easiness in operation.

SULFOXONIUM YLIDE DERIVATIVES AS PROBES FOR CYSTEINE PROTEASE

The present invention relates to compounds of formula I bearing a sulfoxonium ylide moiety as warhead, or salts thereof. Such compounds can be used as activity-based probes for cysteine proteases such as cathepsin X, in methods of detecting cysteine protease activity and in related diagnostic or therapeutic methods.

Designed Negative Feedback from Transiently Formed Catalytic Nanostructures

Highly dynamic and complex systems of microtubules undergo a substrate-induced change of conformation that leads to polymerization. Owing to the augmented catalytic potential at the polymerized state, rapid hydrolysis of the substrate is observed, leading to catastrophe, thus realizing the out-of-equilibrium state. A simple synthetic mimic of these dynamic natural systems is presented, where similar substrate induced conformational change is observed and a transient helical morphology is accessed. Further, augmented catalytic potential of these helical nanostructures leads to rapid hydrolysis of the substrate providing negative feedback on the stability of the nanostructures and realization of an out-of-equilibrium state. This simple system, made from amino acid functionalized lipids, demonstrates a substrate-induced self-assembled state, where the fuel-to-waste conversion leads to the temporal presence of helical nanostructures.

Spontaneous Assembly of Rotaxanes from a Primary Amine, Crown Ether and Electrophile

We report the synthesis of crown ether-ammonium, amide and amine [2]rotaxanes via transition state stabilization of axle-forming reactions. In contrast to the two-step "clipping" and "capping" strategies generally used for rotaxane synthesis, here the components assemble into the interlocked molecule in a single, reagent-less, step under kinetic control. The crown ether accelerates the reaction of the axle-forming components through the cavity to give the threaded product in a form of metal-free active template synthesis. Rotaxane formation can proceed through the stabilization of different transition states featuring 5-coordinate (e.g., SN2) or 4-coordinate (e.g., acylation, Michael addition) carbon. Examples prepared using the approach include crown-ether-peptide rotaxanes and switchable molecular shuttles.

Intermediate reaches reed that Wei new synthetic process of the

The invention provides a novel synthesis process of Darunavir intermediate, N-tertbutyloxycarbonyl-L-phenylalanine is used as a raw material, esterification, condensation, reduction, hydrogenation and reduction amination, and other reactions are carried out for preparing the key intermediate of Darunavir: (2R,3S)-3-(tert-butyloxycarbonyl)amino-1-[(2-methyl propyl)amino]-4-phenyl-2-butanol. The new synthesis process of Darunavir intermediate has the advantages of mild reaction condition, simple operation, and high reaction selectivity and yield, and the process is suitable for industrial production.

BUPRENORPHINE ANALOGS

The present invention is directed to Buprenorphine Analog compounds of the Formula (I), Formula (IA) or Formula (IB) shown below, wherein R1, R2, R8, R3a, R3b, G, X, Z and Y are as defined herein. Compounds of the Invention are useful for treating pain, constipation, and other conditions modulated by activity of opioid and ORL-1 receptors.

A simple synthesis of imide-dipeptides

We report a simple approach to synthesize a new class of imide-dipeptides. This approach is mild, and the starting materials are the easily accessible amino acid derivatives. The imide-dipeptides were synthesized from the coupling of an amide and a 4-nitrophenyl activating ester of an amino acid. The acidic proton of the first amide was removed by 1 equivalent of n-butyl lithium to afford the corresponding amide anion which then reacted with the activating ester to give the desired imide derivatives. Georg Thieme Verlag Stuttgart.

Oxo-ester mediated native chemical ligation: Concept and applications

A direct oxo-ester peptide ligation method has been developed. Through the use of an activated C-terminal para nitrophenyl ester (1), it is possible to achieve direct cysteine ligations (1 + 2 → 4). Peptide substrates incorporating bulky C-terminal amino acids (1) can be accommodated with high reaction efficiency. Copyright

A Procedure for Acylation of Phenols with Free Carboxylic Acids

Acylation of phenols with carboxylic acids is performed in the presence of triethylamine and trimeric phosphonitrile chloride (phosphazene). At optimal ratios of the reactants, phenyl esters of substituted benzoic acids and p-nitrophenyl ester of Boc-phenylalanine are prepared.