5511-73-9

Upstream product

• 85-44-9 phthalic anhydride 
• 72-18-4 L-valine 

Downstream Products

• 111114-10-4 (S)-(3,4-Dimethoxyphenyl)-(2-methyl-1-phthalimidopropyl)-keton 
• 187265-95-8 (1S,5S,6S)-2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyryl]-2-aza-bicyclo[3.1.0]hex-3-ene-6-carboxylic acid methyl ester 
• 187265-96-9 C₂₂H₂₇N₃O₉ 
• 187265-97-0 C₃₄H₄₂N₄O₁₀ 
• 126875-70-5 Valin-N-(4-methylphenyl)hydroxamsaeure 
• 1073666-63-3 ((1E,6E)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2S,2'S)-bis(2-amino-3-methylbutanoate) 
• 908253-01-0 (S)-N¹-phenyl-3-methylbutane-1,2-diamine 
• 882528-81-6 Val-NH-iPr 
• 870533-29-2 (S)-2-amino-N-(4-fluorophenyl)-3-methylbutanamide 
• 1309478-56-5 C₁₁H₁₇FN₂ 
• 3057-81-6 (S)-2-amino-N-tert-butyl-3-methylbutanamide 
• 129473-55-8 (S)-2-amino-3-methyl-N-phenylbutanamide 
• 99529-85-8 C₁₉H₁₈N₂O₃ 
• 1309478-53-2 C₁₉H₁₇FN₂O₃ 

Relevant academic research and scientific papers

Chiral Pool-Based Synthesis of Naphtho-Fused Isocoumarins

A variety of chiral derivatives of benzo[d]naphtho[1,2-b]pyran-6-one were prepared in a single step by Et3N-mediated condensation of homophthalic anhydride with different derivatives of (S)-amino acid chlorides at -5 °C by employing a chiral pool methodology. Chirality 27:951-957, 2015.

Antioxidant activity of new aramide nanoparticles containing redox-active N-phthaloyl valine moieties in the hepatic cytochrome P450 system in male rats

We report the synthesis of aramide nanoparticles containing a chiral N-phthaloyl valine moiety and their antioxidant activities on hepatic contents of cytochrome P450, amidopyrene N-demethylase, aniline-4-hyroxylase and induced the hepatic content of cytochrome b5 and nicotinamide adenine dinucleotide phosphate (NADPH) cytochrome C-reductase. Polymers were obtained as well-separated spherical nanoparticles while highly aggregated particles via H-bonding organization of the aramide-containing pyridine led to a thin layer formation. The effects of the nanoparticles and CCl4 on enzyme activities and thiobarbituric acid reactive substances (TBARS) levels of male rat liver were studied. Pretreatments of rats with the polyamides prior to the administration of CCl4 decreased the hepatic content of the tested enzymes. Doses reduced the toxic effects exerted by (CCl3) upon the liver through inhibition of the cytochrome P450 system. Inhibition of such metabolizing enzymes could reduce the carcinogenic effects of chemical carcinogens.

AMINO ACID DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY DISEASES

The present disclosure provides certain amino acid derivatives that inhibit NF-kB activation and are therefore useful for the treatment of inflammatory diseases. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates

The regiospecific and stereoselective 1,2-migration reaction of dialkyl α-diazophosphonates for the synthesis of β-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)4PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to β-amino (E)-enylphosphonates in moderate to good yields.

Palladium-catalyzed direct intermolecular silylation of remote unactivated C(sp3)-H bonds

An efficient and convenient method has been developed to achieve direct silylation of unactivated remote primary or secondary C(sp3)-H bonds to form C-Si bonds with hexamethyldisilane (HMDS). This method highlights the emerging strategy to transform unactivated methyl or methylene into versatile functional groups in organic synthesis and provides a new method to construct functionalized C-Si bonds for synthetic chemistry.

Trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction: Construction of N,S-acetal quaternary centers

Abstract The trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

Prodrugs of neuraminidase inhibitors

A new class of neuramidase inhibitor prodrugs is provided characterized by a prodrug moiety of a carboxyl group modified to form a carbonyl ethoxy amino acid, a carbonyl ethoxy dipeptide or a carbonyl ethoxy tripeptide, a guanidine group modified to form a carbonyl ethoxy amino acid, a carbonyl ethoxy dipeptide, a carbonyl ethoxy tripeptide; a primary alcohol modified to form an esterified single amino acid, dipeptide or tripeptide of zanavimir of the unaltered therapeutic agent. Exemplary therapeutic agents so modified to form prodrugs include zanavimir, oseltamivir and peramivir. The prodrug has increased oral bioavailability relative to the unaltered neuraminidase inhibitor and is effective in the inhibition of viral infections involving neuraminidase in the viral reproductive cycle.

Unexpected stereoselective synthesis of (Z)-β-alkenyl substituted β-amino phosphonates through β,γ-dihydrogen shift reaction catalyzed by a copper(I) complex and iodine [Cu(MeCN)4]PF 6/I2

A series of dialkyl a-diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN) 4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl a-diazophosphonates gave a mixture of β,γ-dihydrogen shift and 1,2-hydride migration products and afforded β-alk- enyl-substituted β-amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.

Chiron based synthesis of isocoumarins: Reactivity of α-substituted carboxylic acids

The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and α-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with α-chloroacids afforded asymmetric isocoumarins in high yield.

Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp3)-H Bonds

Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp3)-H and C(sp 2)-H bonds of secondary amides included 5-methoxy-8-aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β-C-H methylation or γ-C-H arylation step, the γ-C(sp3)-H amination provided access to complex pyrrolidones from readily available precursors. Copyright