19071-60-4

Upstream product

• 553-90-2 Dimethyl oxalate 
• 3182-95-4 L-Phenylalaninol 
• 95-92-1 oxalic acid diethyl ester 
• 201230-82-2 carbon monoxide 
• 105206-97-1 dimethyl (2S,7S)-3,6-diaza-4,5-dioxo-2,7-dibenzyloctano-1,8-dicarboxylate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 

Downstream Products

• 133485-45-7 (S)-N,N'-bis<1-(chloromethyl)-2-phenylethyl>ethanediamide 
• 133463-88-4 (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole 
• 1019203-00-9 C₂₄H₂₆N₂O₇ 
• 1228318-40-8 N,N'-bis[(1S)-1-benzyl-2-O-(diphenylphosphinite)ethyl]ethanediamide 
• 103747-96-2 (2S)-2-[(2-{[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino}ethyl)amino]-3-phenylpropan-1-ol 
• 1597413-22-3 C₈H₁₁N*ClHO₄*C₂₇H₂₅N₃O₆ 
• 1597413-23-4 C₈H₁₁N*ClHO₄*C₂₇H₂₅N₃O₆ 
• 1597413-15-4 (5S,10S)-5,10-dibenzyl-3,12-dioxa-6,9,18-triazabicyclo[12.3.1]octadeca-1⁽¹⁸⁾,14,16-triene-2,7,8,13-tetraone 

Relevant academic research and scientific papers

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enecarbamates (N-Cbz-protected enamines) and alkyl halides with high regio- and enantioselectivity. The method works for both nonactivated and activated alkyl halides and is able to produce enantiomerically enriched amines with two minimally differentiated α-alkyl substituents. The mild conditions lead to high functional group tolerance, which is demonstrated in the postproduct functionalization of many natural products and drug molecules, as well as the synthesis of chiral building blocks and key intermediates to bioactive compounds.

Manganese Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using Chiral Oxamide Ligands

The asymmetric transfer hydrogenation of ketones using isopropyl alcohol (IPA) as hydrogen donor in the presence of novel manganese catalysts is explored. The selective and active systems are easily generated in situ from [MnBr(CO)5] and inexpensive C2-symmeric bisoxalamide ligands. Under the optimized reaction conditions, the Mn-derived catalyst gave higher enantioselectivity compared with the related ruthenium catalyst.

Novel bis(aminoalcohol)oxalamide organogelators and their diglycolylamide analogs: Evaluation of gelation efficiency in various organic fluids

Three modular types of bis(aminoalcohol)oxalamides (1, 4, and 7) and bis(aminoalcohol)diglycolylamide (8) gelators have been prepared by the reaction of the respective aminoalcohols with oxalyl and digycolyl methylesters as potential low-molecular-weight organogelators. The gelation properties of these amides have been evaluated in various aromatic organic solvents (xylene, toluene, isopropyl benzene, and aromatic ether type organic uids such as anisole or α-phenylethylmethylether) as well as the long-chain aliphatic alcohols (1-hexanol, 1-octanol, 2-octanol, and aromatic 1- phenylethanol). The compounds with sec-butyl and ethyl side chains produce good gelation properties in both aromatic and other organic uids. Furthermore, the common oxalamide linker present in the gelators was replaced by an extended diglycolylamide linker (8) and its behaviors were compared with the benzylic oxalamide analog (3). The gelator (8) gives the best results with aromatic fluid and lauric acid ethyl ester. 1H NMR studies reveal the existence of temperature- dependent network assembly/dissolution equilibrium and produce Kgel. FTIR was employed to see the effect of hydrogen bonding in the formation of gel network. Thermodynamic parameters regarding gel-to-sol transition were collected with van't Hoff relationships.

Organogels as novel carriers for dermal and topical drug delivery vehicles

Aminoalcohol based bis-(aminoalcohol)oxalamides (BAOAs) (1,6-amino alcohol=leucinol, isoleucinol, valinol, phenylglycinol, phenylalaninol and 2-amino-1-butanol) have been explored to develop drug depot systems and illustrated as a novel dermal and topical drug delivery vehicle for non-steroidal anti-inflammatory drug molecules. FAE's (Fatty acid ethyl and isopropyl esters) with different chain lengths, ethyl laurate, ethyl myristate, ethyl palmitate, isopropyl laurate, isopropyl myristate, isopropyl palmitate, have been chosen as they are biocompatible organic fluids used typically in cosmetic industry. Ibuprofen (Ib), acting as a model drug, was entrapped in the supramolecular organogels. The release behavior of Ib molecules in the supramolecular organogels was investigated by using UV–vis spectroscopy. The influence of the organogelator and drug concentration, pH values of the accepting media, and nature of solvent (different FAE's) on the release behavior of Ib was investigated under static conditions. The results indicated that the release rate of Ib from the supramolecular organogels was effectively retarded with an increase of the organogelator concentration. Also, the release rates of Ib increased on increasing the Ib content. Furthermore, the release behavior of Ib was found to be different at various pH values in buffers as accepting media. The study of the release kinetics indicated that the release behavior of Ib was in accord with the Higuchi equation and the diffusion-controlled mechanism involved in the Fickian model. These observations indicate that bis-(aminoalcohol)oxalamides gels may act as delivery vehicles for non-steroidal anti-inflammatory drug molecules and also show that the release profiles for such systems can be fine-tuned by the correct choice of gelator-FAE combination.

Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide-diester functions: Enantiomeric recognition for chiral primary organoammonium perchlorate salts

Four novel C2-symmetric macrocyclic compounds with a pyridine function and possessing amide and ester lingeages were prepared. The enantiomeric discrimination abilities of these macrocycles against α-phenylethylammonium and α-(1-naphthyl)ethylammonium perchlorate salts were measured by standard 1H NMR titration techniques in DMSO-d6. A binding constant ratio of 31 (Kbind(S)/Kbind(R)) for two enantiomers of α-(1-naphthyl)ethylammonium salt with the macrocyclic host (S,S)-4 bearing phenyl arms was observed, which corresponds to an enantiomeric discrimination of approximately 94%. Molecular dynamic calculations were performed for some of the supramolecular complexes to in order to gain insight into the mode of molecular recognition between the macrocyclic compounds and ammonium salts; these results were consistent with experimental observations, which may be relevant to those in biochemical processes occurring in organisms.

Asymmetric conjugate addition to cyclic enone catalyzed by Cu-NHC complexes with C2 symmetry

A series of chiral, C2 symmetric tridentate N-heterocyclic carbene precursors, containing two N-functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclo

C2 symmetric synthesis of Bis(amino alcohol)oxalamides and its catalytic activity

The aim of this study is to evaluate C2 symmetric synthesis of bis(amino alcohol)oxalamides and the catalytic activity diethyl zinc to benzaldehyde. Syntheses of diamidediols were achieved nearly quantitatively by reacting oxalic acids methyl esters with amino alcohols directly in a single step reactions and mild conditions. Four modular and rigid diamidediols having C2-symmetry were synthesized forming oxalic moiety main core. The catalytic effects of the N,N′-bis[(1R)-1-ethyl-2- hydroxyethyl] ethanediamide, N,N′-bis[(1S)-1-benzyl-2-hydroxyethyl]- ethanediamide, N,N′-bis[(1S)-1-isobutyl-2-hydroxyethyl]ethanediamide and N,N′-bis[(1S)-1-secbutyl-2-hydroxyethyl]ethanediamide were tested and also N,N′-bis[(1S)-1-benzyl-2-hydroxyethyl]ethanediamide, N,N′- bis[(1S)-1-isobutyl-2-hydroxyethyl]ethanediamide were synthesized. The catalytic activity of C2-symmetric diamidediols on the addition reaction of diethyl zinc to benzaldehyde and effects of alkyl moiety bonded to stereogenic center on enantioselectivity were conducted out.

Novel C2-symmetric macrocycles bearing diamide-diester groups: Synthesis and enantiomeric recognition for primary alkyl ammonium salts

(Chemical Equation Presented) We synthesized a series of novel macrocycles with diamide-diester groups (S,S)-1, (S,S)-2, (S,S)-3, and (R,R)-1, derived from dimethyloxalate and amino alcohols by high dilution technique, and evaluated enantiomeric recognition properties of these macrocycles toward primary alkyl ammonium salts by 1H NMR titration. Taking into account the host employed, important differences were observed in the Ka values of (R)-Am and (S)-Am for (S,S)-1 and (R,R)-1 hosts, KS/KR = 5.55 and KR/KS = 3.65, ΔΔGo = 0.43 and -0.32 kJ mol-1, respectively. There seems a general tendency for the host to include the guests with the same absolute configuration.

Synthesis of new polydentate oxalamide-based ligands as chiral catalysts for the enantioselective addition of diethylzinc to benzaldehyde

New polydentate oxalamide-based ligands have been studied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde.

Chiral bis(amino alcohol)oxalamides as ligands for asymmetric catalysis. Ti(IV) catalyzed enantioselective addition of diethylzinc to aldehydes

Several chiral bis(aminoalcohol)oxalamides with C2-symmetry have been prepared and used as ligands for the enantioselective addition of diethylzinc to aromatic and aliphatic aldehydes. The reaction proceeds in the presence of titanium isopropoxide to give the corresponding (S)-alcohols with ee up to 78%. In the absence of Ti(IV), the alcohols with the opposite configuration are obtained.