56776-41-1

Upstream product

• 121598-58-1 (Z)-2-Isocyanato-but-2-enoic acid methyl ester 
• 75-65-0 tert-butyl alcohol 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 79-36-7 dichloroacethyl chloride 
• 475288-42-7 Boc-(E)-ΔAbu(β-Br)-OMe 
• 475288-43-8 Boc-(Z)-ΔAbu(β-Br)-OMe 
• 1242683-60-8 methyl (E)-2-(tert-butoxycarbonylamino)-3-iodo-but-2-enoate 
• 1084941-27-4 Boc-Z-ΔAbu(β-I)-OMe 
• 58561-08-3 (S)-methyl 2-(((tert-butoxy)carbonyl)amino)butanoate 
• 63096-22-0 C₁₀H₁₈ClNO₄ 
• 60538-19-4 N-(tert-butoxycarbonyl)-l-threonine methyl ester 
• 619-80-7 4-nitrobenzamide 
• 125564-99-0 erythro Boc-3-fluoroglutamate α methyl ester 
• 100-39-0 benzyl bromide 

Downstream Products

• 34329-73-2 methyl 3-bromo-2-oxobutanoate 
• 63658-16-2 (Z)-methyl 2-((tertbutoxycarbonyl)amino)but-2-enoate 
• 58561-08-3 (S)-methyl 2-(((tert-butoxy)carbonyl)amino)butanoate 
• 112392-65-1 methyl (2R) 2-<(1,1-dimethylethoxy)carbonyl amino>butyrate 

Relevant academic research and scientific papers

SUBSTITUTED HETEROCYCLICS WITH THERAPEUTIC ACTIVITY IN HIV

Substituted heterocyclic substituted pyrrole carboxamide compounds such as those represented by Formula I or Formula II are provided herein. Such compounds, or pharmaceutically acceptable salts thereof, can be used in the treatment of HIV infection and re

Preclinical Optimization of gp120 Entry Antagonists as anti-HIV-1 Agents with Improved Cytotoxicity and ADME Properties through Rational Design, Synthesis, and Antiviral Evaluation

We previously reported a milestone in the optimization of NBD-11021, an HIV-1 gp120 antagonist, by developing a new and novel analogue, NBD-14189 (Ref1), which showed antiviral activity against HIV-1HXB2, with a half maximal inhibitory concentr

Synthesis of new β-amidodehydroaminobutyric acid derivatives and of new tyrosine derivatives using copper catalyzed C-N and C-O coupling reactions

Several β-amidodehydroaminobutyric acid derivatives were prepared from N,C-diprotected β-bromodehydroaminobutyric acids and amides by a copper catalyzed C-N coupling reaction. The best reaction conditions include the use of a catalytic amount of CuI, N,N'-dimethylethylenediamine as ligand and K 2CO3 as base in toluene at 110 C. The stereochemistry of the products was determined using NOE difference experiments and the results obtained are in agreement with an E-stereochemistry. Thus, the stereochemistry is maintained in the case of the E-isomers of β-bromodehydroaminobutyric acid derivatives, but when the Z-isomers were used as substrates the reaction proceeds with inversion of configuration. The use of β- bromodehydrodipeptides as substrates was also tested. It was found that the reaction outcome depend on the stereochemistry of the β- bromodehydrodipeptide and on the nature of the first amino acid residue. The products isolated were the β-amidodehydrodipeptide derivatives and/or the corresponding dihydropyrazines. The same catalytic system (CuI/N,N'- dimethylethylene diamine) was used in the C-O coupling reactions between a tyrosine derivative and aryl bromides. The new O-aryltyrosine derivatives were isolated in moderate to good yields. The photophysical properties of two of these compounds were studied in four solvents of different polarity. The results show that these compounds after deprotection can be used as fluorescence markers.

Synthesis and electrochemical behaviour of β-halodehydroamino acid derivatives

Several new β,β-dihalo and β-halo-β-substituted dehydroalanines and dehydrodipeptides were synthesized by reacting the corresponding dehydroamino acid derivative with a N-halosuccinimide or in the case of β,β-di-iododehydroalanines with iodine. The results obtained confirmed that the stereochemical outcome of the halogenation reaction with β-substituted dehydroamino acids depends on the substrate. Thus, an increase Z-stereoselectivity was found when the β-phenyldehydroalanines were used as substrates and when these compounds were N-protected with 4-tolylsulfonyl or with carbamates. From this study, it is also possible to conclude that when N-iodosuccinimide was used as reagent a much higher Z-stereoselectivity is found. The electrochemical behaviour of the halogenated dehydroamino acids was studied by cyclic voltammetry. The results show a shift in the reduction peak to higher potentials of the β-halogenated dehydroamino acids when compared with the corresponding non-halogenated derivatives. As expected, the β,β-dihalodehydroalanines exhibit higher peak potentials than β-halo-β-substituted dehydroalanines and the bromo derivatives have lower peak potentials when compared with the corresponding iododehydroamino acids. Controlled potential electrolysis of several β-halo-β-substituted dehydroamino acids afforded the corresponding dehalogenated dehydroamino acids as mixtures of their E and Z-isomers. In all cases, the major isomer isolated results from dehalogenation without isomerization. These new results show that electrochemical reduction constitutes a valuable method for the synthesis of the E-isomer of β-substituted dehydroalanines. Springer-Verlag 2010.

Stereoselective syntheses of (E)-α,β-didehydroamino acid and peptide containing its residue utilizing oxazolidinone derivative

Reaction of methyl N-Boc-N-phenoxycarbonylglycinate with various aldehydes afforded the corresponding cis-4,5-oxazolidinone derivatives, which were effectively converted to (E)-α,β-didehydroamino acids by means of a base. Furthermore, N-deprotection of the oxazolidinone derivatives and subsequent coupling reaction with Boc-amino acid furnished the corresponding dipeptides, which were transformed to dipeptide containing α,α- didehydroamino acid with high E selectivity.

FIVE-MEMBERED HETEROCYCLIC DERIVATIVE

The present invention relates to a compound represented by formula (I): a salt of the compound, or a solvate of the compound or the salt; a drug containing any of the compounds, the salts, and the solvates; a preventive and/or therapeutic agent for an ischemic disease containing any of the compounds, the salts, and the solvates; and a platelet coagulation inhibitor containing any of the compounds, the salts, and the solvates. The compound of the present invention is useful as a strong platelet coagulation inhibitor without inhibiting COX-1 or COX-2.

Stereoselective syntheses of (E)-α,β-dehydroamino acids and (E)-α,β-dehydropeptides by stereospecific dehydration with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)

Highly stereoselective syntheses of (E)-α,β-dehydroamino acids and (E)-α,β-dehydropeptides have been achieved in good yields by stereospecific dehydration of threo-β-hydroxy-α-amino acid derivatives using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC

Design and synthesis of carboxylate inhibitors for matrix metalloproteinases

A series of carboxylate compounds were prepared from Nα-substituted 2,3-diaminopropionic acid and were tested for efficacy as matrix metalloproteinase (MMP) inhibitors. During modeling of the initial compound 10a, we utilized three-dimensional

Design and use of an oxazolidine silyl enol ether as a new homoalanine carbanion equivalent for the synthesis of carbon-linked isosteres of O- glycosyl serine and N-glycosyl asparagine

A trimethylsilyl enol ether carrying the N-Boc 2,2-dimethyloxazolidine ring was designed to serve as a synthetic equivalent of the homoalanine carbanion for the introduction of the α-amino acid side chain at the anomeric carbon of sugars. This new functio