54895-12-4

Usage

Uses

Used in Pharmaceutical Industry:
BOC-DL-VALINE is used as a synthesis intermediate for the preparation of amino acid ester homocamptothecin analogs. These analogs exhibit anti-tumor properties, making them valuable in the development of novel cancer treatments. The BOC group in BOC-DL-VALINE is essential for protecting the amino group during the synthesis process, ensuring the stability and reactivity of the final product.

Upstream product

• 75-30-9 2-iodo-propane 
• 4530-20-5 BOC-glycine 
• 169556-48-3 rac-tert-butyl (1-hydroxy-3-methylbutan-2-yl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 516-06-3 D,L-valine 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 
• 117681-86-4 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate 
• 117049-11-3 2-tert-Butoxycarbonylamino-3-methyl-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 111652-06-3 tert-butyl (tert-butoxycarbonyl)valinate 

Downstream Products

• 50903-49-6 2-tert-Butoxycarbonylamino-3-methyl-butyric acid pentafluorophenyl ester 
• 131971-63-6 tert-butyl N-(1-methoxy-2-methylpropyl)carbamate 
• 117049-11-3 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (S)-2-<(tert-butoxycarbonyl)amino>-3-methylbutanoate 
• 33419-01-1 H-Val-OH p-toluenesulfonic acid salt 
• 672959-49-8 tert-butyl [1-(2-methylphenylcarbamoyl)-1-isoprpyl-methyl]-carbamate 
• 891789-87-0 C₁₇H₂₃N₃O₃ 
• 133010-02-3 1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-methylpropyl)carbamate 
• 1161408-63-4 2-(Boc-amino)-N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-3-methyl-butyramide 
• 1204929-93-0 [1-(N'-benzoyl-hydrazinocarbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 4333-20-4 5-isopropyl-3-phenyl-2-thioxo-imidazolidin-4-one 

Relevant academic research and scientific papers

A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids

Abstract: –A simple trituration method for the synthesis of 2-substituted benzothiazoles derived from N-protected amino acids and 2-aminothiophenol using molecular iodine as a mild Lewis acid catalyst has been proposed. The reaction occurs in one step for 20–25 min in solve-free conditions and provides the target products in excellent yields.

HMOX1 inducers

The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.

Amino acid conjugated antimicrobial drugs: Synthesis, lipophilicity- activity relationship, antibacterial and urease inhibition activity

Present work describes the in vitro antibacterial evaluation of some new amino acid conjugated antimicrobial drugs. Structural modification was attempted on the three existing antimicrobial pharmaceuticals namely trimethoprim, metronidazole, isoniazid. Twenty one compounds from seven series of conjugates of these drugs were synthesized by coupling with some selected Boc-protected amino acids. The effect of structural features and lipophilicity on the antibacterial activity was investigated. The synthesized compounds were evaluated against five standard American type culture collection (ATCC) i.e. Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi strains of bacteria. Our results identified a close relationship between the lipophilicity and the activity. Triazine skeleton proved beneficial for the increase in hydrophobicity and potency. Compounds with greater hydrophobicity have shown excellent activities against Gram-negative strains of bacteria than Gram-positive. 4-amino unsubstituted trimethoprim-triazine derivative 7b have shown superior activity with MIC = 3.4 μM (2 μg/mL) for S. aureus and 1.1 μM (0.66 μg/mL) for E. coli. The synthesized compounds were also evaluated for their urease inhibition study. Microbial urease from Bacillus pasteurii was chosen for this study. Triazine derivative 7a showed excellent inhibition with IC50 = 6.23 ± 0.09 μM. Docking studies on the crystal structure of B. pasteurii urease (PDB ID 4UBP) were carried out.

Enantioselective Synthesis of Quaternary Δ4- and Δ5-Dehydroprolines Based on a Two-Step Formal [3+2] Cycloaddition of α-Aryl and α-Alkyl Isocyano(thio)acetates with Vinyl Ketones

A divergent synthesis of optically active quaternary Δ4- and Δ5-dehydro prolines is developed based on the first catalytic enantioselective conjugate addition of α-substituted isocyano(thio)acetates to vinyl ketones that is general for both α-aryl and α-alkyl isocyano(thio)acetates. The new tetrasubstituted C?N stereocenter is formed without the need of any metal salt due to a bifunctional tertiary amine/squaramide catalyst, featuring a bulky polyaryl sidearm and an unusually short squaramide diamide H???H interatomic distance in the solid state.

Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes

N-Boc-α-amino aldehydes are shown to be excellent partners in cross-benzoin reactions with aliphatic or heteroaromatic aldehydes. The chemoselectivity of the reaction and the facial selectivity on the amino aldehyde allow cross-benzoin products to be obtained in good yields and good diastereomeric ratios. The developed method is utilized as the key step in a concise total synthesis of d-arabino-phytosphingosine.

Liquid chromatographic resolution of amino acid esters of acyclovir including racemic valacyclovir on crown ether-based chiral stationary phases

Valacyclovir, a potential prodrug for the treatment of patients with herpes simplex and herpes zoster, and its analogs were resolved on two chiral stationary phases (CSPs) based on (3,3′-diphenyl-1,1′-binaphthyl)-20-crown-6 covalently bonded to silica gel. In order to find out an appropriate mobile phase condition, various mobile phases consisting of various organic modifiers in water containing various acidic modifiers were applied to the resolution of valacyclovir and its analogs. When 30% acetonitrile in water containing any of 0.05 M, 0.10 M, or 0.15 M perchloric acid was used as a mobile phase, valacyclovir and its analogs were resolved quite well on the two CSPs with the separation factors (α) in the range of 2.49～6.35 and resolutions (RS) in the range of 2.95 ～ 12.21. Between the two CSPs, the CSP containing residual silanol protecting n-octyl groups on the silica surface was found to be better than the CSP containing residual silanol groups.

Enantiomeric resolution of α-amino acid derivatives on two diastereomeric chiral stationary phases based on chiral crown ethers incorporating two different chiral units

Two diastereomeric chiral stationary phases (CSPs) were applied to the liquid chromatographic resolution of various racemic a-amino methyl esters, α-amino N,N-diethylamides and α-amino N-propylamides. The CSP incorporating (R)-3,3' -diphenyl-1,1' -binaphtyl and (R,R)-tartaric acid unit as chiral barriers did not show any chiral recognition. In contrast, the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit as chiral barriers was found to show excellent chiral recognition especially for the two enantiomers of a-amino N-propylamides. Some of a-amino methyl esters and α-amino N,N-diethylamides were also resolved on the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit. From these results it was concluded that the two chiral units composing the diastereomeric CSPs can show "matched" or "mismatched" effect on the chiral recognition according to their absolute stereochemistry.

Enzymatic removal of carboxyl protecting groups. 1. Cleavage of the tert-butyl moiety

(Chemical Equation Presented) A recent discovery that a certain amino acid motif (GGG-(A)X-motif) in lipases and esterases determines their activity toward tertiary alcohols prompted us to investigate the use of these biocatalysts in the mild and selective removal of tert-butyl protecting groups in amino acid derivatives and related compounds. An esterase from Bacillus subtilis (BsubpNBE) and lipase A from Candida antarctica (CAL-A) were identified as the most active enzymes, which hydrolyzed a range of tert-butyl esters of protected amino acids (e.g., Boc-Tyr-OtBu, Z-GABA-OtBu, Fmoc-GABA-O tBu) in good to high yields and left Boc, Z, and Fmoc-protecting groups intact.

Chiral gelators constructed from 11-aminoundecanoic (AUDA), lauric and amino acid units. Synthesis, gelling properties and preferred gelation of racemates vs. the pure enantiomers

A new class of efficient low molecular weight gelator molecules has been designed by combining 11-aminoundecanoic acid (AUDA), lauric acid and aromatic and aliphatic amino acid units in the same molecule. This yields a special class of fatty acid amphiphiles with core chiral centres and hydrogen bonding sites. Some of the compounds with terminal carboxylic acid and sodium carboxylate functions exhibited ambidextrous gelation properties, being able to form gels both with highly polar solvents (water, DMSO) and also with highly lipophilic solvents, including two hydrocarbon fuels. At variance with several recent observations that the enantiomers are generally more efficient gelators than the corresponding racemates, some of the racemic gelators prepared in this work were found to be capable of gelling up to 16 times larger volumes of certain solvents than the pure enantiomers. Temperature-dependent FTIR and 1H NMR studies of the gels formed by derivatives with terminal carboxylic acid groups and lipophilic solvents revealed that intermolecular hydrogen bonding between amidic and carboxylic acid units was involved in the self-assembly of gel aggregates. Additional strong stabilization of the aggregates was observed in the gelators possessing terminal sodium carboxylate groups, and this was attributed to the electrostatic and ion-dipole interactions between the sodium carboxylate groups. This additional stabilization appears to be responsible for considerably higher thermal stability of the latter gels in relation to those formed by gelators with terminal carboxylic acid groups. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Efficient electrochemical deprotection of carboxylic and amino acids from their 2-(hydroxymethyl)-1,3-dithiane (dim) esters

formula presented Carboxylic acids and amino acids are electrochemically deprotected from their 2-(hydroxymethyl)-1,3-dithiane (Dim) esters.