67106-22-3

Usage

Uses

Used in Organic Synthesis:
(S)-tert-butyl 1-(benzylamino)-3-methyl-1-oxobutan-2-ylcarbamate is used as a reagent in organic synthesis for its ability to participate in asymmetric synthesis reactions, which are crucial for creating enantiomerically pure compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-tert-butyl 1-(benzylamino)-3-methyl-1-oxobutan-2-ylcarbamate is used as a building block for the development of new pharmaceuticals, taking advantage of its unique structural features and reactivity.
Used in Drug Discovery and Development:
(S)-tert-butyl 1-(benzylamino)-3-methyl-1-oxobutan-2-ylcarbamate has potential applications in drug discovery and development due to its structural complexity and the possibility of creating novel bioactive molecules through its use in chemical synthesis.
Used in the Production of Chemical Compounds:
This carbamate derivative is also utilized in the production of other chemical compounds, where its unique functional groups and reactivity can be harnessed to create a variety of synthetic products through different synthetic pathways.

Upstream product

• 3392-12-9 Boc-Val-ONSu 
• 3287-99-8 benzylamine hydrochloride 
• 100-46-9 benzylamine 
• 66866-46-4 C₁₅H₂₇NO₆ 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1446274-25-4 (S)-Se-((9H-fluorenyl)methyl) 2-((tert-butoxycarbonyl)amino)-3-methylbutaneselenoate 
• 72-18-4 L-valine 
• 66447-55-0 ((S)-1-benzylcarbamoyl-2-methyl-propyl)-carbamic acid tert-butyl ester 
• 1033037-50-1 tert-butyl (S)-(1-chloro-3-methyl-1-oxobutan-2-yl)carbamate 
• 13734-41-3 t-Boc-L-valine 

Downstream Products

• 873017-34-6 {(3S,6S,13S)-13-[(1S,3R)-3-((S)-1-Benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-hydroxy-butyl]-3-methyl-2,5-dioxo-1,4-diaza-cyclotridec-6-yl}-carbamic acid tert-butyl ester 
• 1201901-59-8 (S)-2-amino-N-benzyl-3-methylbutyramide hydrochloride 
• 1201890-83-6 N-(tert-butoxycarbonyl)-L-valine benzylthioamide 
• 1375257-26-3 (S)-3-acetyl-1-benzyl-4-isopropylimidazolidin-2-one 
• 1375257-34-3 (S)-1-benzyl-3-[(S)-3-hydroxy-3-phenylpropanoyl]-4-isopropylimidazolidin-2-one 
• 1056670-98-4 (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-(naphthalen-1-ylmethoxy)-hexanoic acid ((S)-1-benzylcarbamoyl-2-methylpropyl)-amide trifluoroacetate 
• 1056681-45-8 C₃₉H₅₃N₃O₇ 
• 1056675-55-8 (2S,4S,5S)-5-azido-6-(3-((1RS)-1-(t-butoxycarbonylamino)ethyl)benzyloxy)-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)-amide 
• 1056671-27-2 (2S,4S,5S)-5-amino-6-(3-(1-(t-butoxycarbonylamino)ethyl)benzyloxy)-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)-amide 
• 1056674-73-7 C₃₅H₅₁N₃O₇ 
• 1056674-68-0 [(1S,2S,4S)-4-((S)-1-benzylcarbamoyl-2-methylpropylcarbamoyl)-1-benzyloxymethyl-2-hydroxy-5-methylhexyl]-carbamic acid tert-butyl ester 
• 1056674-78-2 acetic acid (1S,3S)-3-((S)-1-benzylcarbamoyl-2-methylpropylcarbamoyl)-1-((S)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-4-methylpentyl ester 
• 1056670-83-7 (2S,4S,5S)-5-amino-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)amide trifluoroacetate 
• 1056674-63-5 (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)amide 

Relevant academic research and scientific papers

Cytotoxic activity of synthetic chiral amino acid derivatives

Cancer is a chronic degenerative disease considered one of the most important causes of death worldwide. In this context, a series of dual-protected amino acid derivatives was synthesized and evaluated as potential novel anticancer agents. The 40 derivatives were prepared in up to three reaction steps. The cytotoxic activities were screened in vitro against a panel of tumor and non-tumor cells using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among the synthesized derivatives, three of them showed promising activity against cancer cells with half-maximal inhibitory concentration (IC50) ranging between 1.7-6.1 μM. The most promising derivative, bearing both a lipophilic N-alkyl diamine moiety and a protected amino acid scaffold showed a selectivity index of 3.4 towards tumor cells. The N-alkyl diamine moiety seems to play a crucial role in the enhancement of the anticancer activity. On the other hand, the incorporation of an amino acid scaffold resulted in increase in the selectivity towards cancer cell lines.

Dual-protected amino acid derivatives as new antitubercular agents

Tuberculosis is an infectious disease with high incidence and growing drug-resistant rates. In an attempt to develop new antitubercular agents, 35 compounds were synthesized, most of them bearing a carbamate and enantiopure amino acid moiety. These compounds had their activity evaluated toward a Mycobacterium tuberculosis strain (ATCC 27294) and cytotoxicity against fibroblast MRC-5 cells (ATCC CCL-171). Three of the prepared derivatives presented a good antimicrobial inhibition and two of them a moderate cytotoxicity. The lipophilicity seems to play a vital role in the cell growth activity, with best results for the derivatives with a higher logP.

[...] - Orn (ClCH2NH) - AA - benzylamine, its synthesis, activity and application (by machine translation)

The invention discloses the following formula of 13 for β - Carboline -3 - formyl - Orn (ClCH2 NH) - AA - NHCH2 C6 H5 (In the formula AA is selected from L - Arg, L - Asn, L - Asp, L - Glu, L - Gly, L - Ile, L - Leu, L - Met, L - Phe, L - Pro, L - Thr, L - Trp, L - Val residue), discloses a process for their preparation, discloses their inhibition of tumor cell growth, therefore this invention discloses their use as anti-tumor medicament. (by machine translation)

l-tert-Leucine-Derived AmidPhos-Silver(I) Chiral Complexes for the Asymmetric [3+2] Cycloaddition of Azomethine Ylides

The l-tert-leucine-derived AmidPhos/silver(I) catalytic system has been developed for the asymmetric [3+2] cycloaddition of azomethine ylides with electronic-deficient alkenes with or without Et3N. Under optimal conditions, highly functionalized endo-4-pyrrolidines were obtained with modest to high yields (up to 99% yield) and enantioselectivities (up to 98% ee).

Ag2CO3/CA-AA-amidphos multifunctional catalysis in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides

The new Ag2CO3/CA-AA-amidphos complexes have been demonstrated as highly efficient multifunctional catalysts in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. Under optimal conditions, highly functionalized endo-4 pyrrolidines were obtained with excellent yields (up to 99% yield) and enantioselectivities (up to 96% ee).

Highly modular dipeptide-like organocatalysts for direct asymmetric aldol reactions in brine

A novel series of dipeptide-like organocatalysts derived from proline, amino acids and primary amines have been prepared for direct asymmetric aldol reactions between various aromatic aldehydes and acetone to afford aldol products in good yields (up to 82%) and moderate enantioselectivities (up to 67% ee) with only 1 mol% of catalyst-loading in brine. Under the same conditions, the direct asymmetric aldol reactions of aromatic aldehydes and cyclohexanone give aldol products with high yields (up to 91%) and moderate to good enantioselectivities (up to 88% ee) and excellent diastereoselectivities (up to 99% dr). These organocatalysts are easily synthesized from commercially available materials in multi-gram scale with high modularity in their structural and stereogenic properties.

New chiral zwitterionic phosphorus heterocycles: Synthesis, structure, properties and application as chiral solvating agents

A family of new chiral zwitterionic phosphorus-containing heterocycles (zPHC) have been derived from methylene-bridged bis(imidazolines). These structures were unambiguously determined, including single-crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed as a new class of chiral solvating agents for the enantiodifferentiation of chiral carboxylic and sulfonic acids by NMR spectroscopy. The stoichiometry and binding constants for the donor-acceptor complexes formed were established by NMR titration methods. A convenient synthetic approach to a new class of chiral zwitterionic phosphorus-containing heterocycles starting from methylene-bridged bis(imidazolines) was designed and executed. Stability and properties of the synthesized compounds were investigated. The applicability of the designed compounds as chiral solvating agents for the determination of the enantiomeric excesses of chiral acids was demonstrated. Copyright

Se -(9-fluorenylmethyl) selenoesters; Preparation, reactivity, and use as convenient synthons for selenoacids

Se-(9-Fluorenylmethyl) selenoesters are readily prepared, stable precursors to selenocarboxylates, which they liberate on treatment with DBU. Fm selenoesters are compatible with the use of TFA for the removal of Boc groups and with simple peptide bond for

Reversal of selectivity in acetate aldol reactions of N-acetyl-(S)-4- isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one

Synergistic effects of the exo- and endocyclic chiral centers of an imidazolidinone-based auxiliary were investigated in the perspective of acetate aldol reactions. The reversal in diastereoselectivity was accomplished by lithium and titanium enolate reactions, which proceed through proposed open and closed transitions states, respectively. The aldol adducts were used in the stereoselective synthesis of fluoxetine.

Sodium methoxide: A simple but highly efficient catalyst for the direct amidation of esters

A simple NaOMe catalyst provides superior accessibility to a wide variety of functionalized amides including peptides through direct amination of esters in an atom-economical and environmentally benign way.