35193-63-6

Usage

Uses

Used in Asymmetric Synthesis:
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used as a chiral ligand for hydrocarboxylation reactions, facilitating the formation of chiral molecules with a specific configuration. This is particularly important in the pharmaceutical industry, where the stereochemistry of a molecule can significantly impact its biological activity and efficacy.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is used as a chiral ligand for the resolution of racemic amines, which are often difficult to separate. The use of this chiral acid allows for the production of enantiomerically pure compounds, which can be crucial for the development of effective and safe drugs.
Used in Catalyst Development:
1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is also used in the development of catalysts for asymmetric hydrocarboxylations and dipolar cycloadditions. Palladium and rhodium derivatives of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate have been employed to improve the selectivity and efficiency of these reactions, leading to the synthesis of complex molecules with high enantiomeric purity.
Overall, 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate is a versatile and valuable compound in the fields of asymmetric synthesis, pharmaceuticals, and catalyst development, playing a crucial role in the production of enantiomerically pure compounds and the development of efficient catalytic systems.

Upstream product

• 124583-86-4 (R)-1,1'-binaphthalene-2,2'-diyl phosphoric acid chloride 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 602-09-5 1,1'-bi-2-naphthol 
• 35193-63-6 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 124583-86-4 (+/-)-1,1'-Binaphthyl-2,2'-diyl phosphorochloridate 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 35193-63-6 (R)-1,1'-binaphthyl-2,2'-phosphoric acid 
• 35193-63-6 (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate 

Relevant academic research and scientific papers

Hydrophilic interior between hydrophobic regions in inverse bilayer structures of cation-1,1′-binaphthalene-2,2′-diyl phosphate salts

A series of 1,1′-binaphthalene-2,2′-diyl phosphate (BNPPA -) salts have been synthesized. Their crystal packings show a separation of the hydrophobic naphthyl and hydrophilic (RO)2PO 2- phosphate/cation/solvate regions. Hydrogen bonding in the latter is the driving force for "inverse bilayer" formation, with a hydrophilic interior exposing the hydrophobic binaphthyl groups to the exterior. Stacking of the inverse bilayers occurs less through π-π and more through CH...π interactions between the naphthyl groups, which correlates with the formation of thin crystal plates along the stacking direction. Cations used with R- or rac-BNPPA- are protonated isonicotin-1-ium amide (1), isonicotin-1-ium acid (2), guanidinium (3), the metal complexes trans-tetraammine-dimethanol-copper(II) (4), trans-diaqua-tetramethanol-copper(II) (5) and cis-diaqua-bis(ethylene diamine)-nickel(II) (6). Crystallization occurs with inclusion of water and methanol solvent molecules, except in 2. Starting from R-BNPPA, inversion takes place with calcium acetate to give 1 as the racemate. 2 is crystallized as the R-BNPPA salt. The inversion-symmetrical complex trans-[Cu(H2O) 2(CH3OH)4]2+ in 5 has Cu-OH 2 bond lengths of 1.937(4) A, and Cu-O(methanol) of 2.112(4) and 2.167(4) A, corresponding to a compressed tetragonal geometry. the Royal Society of Chemistry the Centre National de la Recherche Scientifique 2006.

FUSED RING PYRIMIDONE DERIVATIVES FOR USE IN THE TREATMENT OF HBV INFECTION OR OF HBV-INDUCED DISEASES

Provided are compounds according to any of Formula (I-1) to (I-7), pharmaceutical compositions comprising at least one of said compounds, their use as a medicament, and their use in treating chronic hepatitis B virus (HBV) infection. Methods for preparing compounds according to any of Formula (I-1) to (I-7) are also provided.

Flash production of organophosphorus compounds in flow

Flow synthesis techniques have received a significant amount of attention due to their high productivity. However, when reaction condition is heterogeneous, it is usually difficult to adapt it to flow synthesis. Herein, by selecting appropriate reagents, the synthesis of phosphate esters, which is commonly heterogeneous, was made homogeneous, enabling synthesis in flow systems. In addition, reaction rate was accelerated compared to the batch system. It was demonstrated that not only can the high productivity of flow synthesis be achieved in flow, but also high productivity can be achieved by accelerating the reaction. Finally, we demonstrated the synthesis of the Akiyama-Terada catalyst, a chiral organocatalysts, in a short period.

Asymmetric ketone hydroboration catalyzed by alkali metal complexes derived from BINOL ligands

The ability of alkali metal complexes featuring functionalized BINOL-derived ligands to catalyze ketone hydroboration reactions was explored. The reduced products were formed in excellent yields and with variable enantioselectivities dependent upon the nature of the ligand and the alkali metal cation.

Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).

Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis

Diquats with extremely high racemization barriers with ΔG≠theor of 233 kJ mol?1 at 180 °C are described. Reported configurational robustness is due to a combination of two structural features: the rigid o-xylylene tether connecting the nitrogen atoms and the presence of two substituents in the bay region of the bipyridinium scaffold. The straightforward synthesis of diquats, plus facile resolution and derivatization make them attractive for chiral application studies. This is demonstrated by: 1) synthesis of the first non-racemic diquat dyes with pronounced chiroptical properties, and 2) capability of diquats to interact stereospecifically with chiral molecules. This suggests potential for diquat derivatives to be used as chiral selectors in separation methods.

Chiral separation on various modified amino alcohol-derived HPLC chiral stationary phases

3,5-Dinitrobenzoyl chloride was previously used for the preparation of (R)-phenylglycinol- and (S)-leucinol-derived chiral stationary phases. In this study, 3,5-bis(trifluoromethyl)benzoyl chloride, 2-furoyl chloride, 2-theonyl chloride, 10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride, diphenylcarbamoyl chloride, and 1-adamantanecarbonyl chloride were used to prepare six new phenylglycinol-derived chiral stationary phases (CSPs) and five new leucinol-derived CSPs. Using these 11 CSPs, chiral separation of nine π-acidic amino acid derivatives and five π-basic compounds was performed, and the separation results were compared. An adamantyl-derived CSP showed good separation.

Direct Asymmetric Friedel-Crafts Reaction of Naphthols with Acetals Catalyzed by Chiral Bronsted Acids

The Friedel-Crafts method synthesis of chiral ethers from various acetals and naphthols catalyzed by chiral Bronsted acids with acetic acid as an effective additive is described. We found that the chiral phosphoric acid (R)-TRIP could efficiently catalyze the asymmetric Friedel-Crafts reaction of naphthols with acetals affording chiral ethers in good enantioselectivity and yield.

Synthesis of novel chiral phosphoric acid-bearing two acidic phenolic hydroxyl groups and its catalytic evaluation for enantioselective Friedel-Crafts alkylation of indoles and enones

A novel chiral phosphoric acid catalyst bearing two acidic phenolic hydroxyl groups was synthesized. Its catalytic activity as a chiral Br?sted acid has been examined in the enantioselective Friedel-Crafts alkylation of indoles and enones as a model reaction. In comparison with the other chiral phosphoric acid catalysts, the reaction catalyzed by the novel chiral catalyst afforded the desired 3-substituted indoles in a higher enantioselectivity (up to 69% ee).

Enantiomeric separations of chiral sulfonic and phosphoric acids with barium-doped cyclofructan selectors via an ion interaction mechanism

New cyclofructan-6 (CF6)-based chiral stationary phases (CSPs) bind barium cations. As a result, the barium-complexed CSPs exhibit enantioselectivity toward 16 chiral phosphoric and sulfonic acids in the polar organic mode (e.g., methanol or ethanol mobile phase containing a barium salt additive). Retention is predominantly governed by a strong ionic interaction between the analyte and the complexed barium cation as well as hydrogen bonding with the cyclofructan macrocycle. The log k versus log [X], where [X] = the concentration of the barium counteranion, plots for LARIHC-CF6-P were linear with negative slopes demonstrating typical anion exchange behavior. The nature of the barium counteranion also was investigated (acetate, methanesulfonate, trifluoroacetate, and perchlorate), and the apparent elution strength was found to be acetate > methanesulfonate > trifluoroacetate > perchlorate. A theory based upon a double layer model was proposed wherein kosmotropic anions are selectively adsorbed to the cyclofructan macrocycle and attenuate the effect of the barium cation. van't Hoff studies for two analytes were conducted on the LARIHC-CF6-P for three of the barium salts (acetate, trifluoroacetate, and perchlorate), and the thermodynamic parameters governing retention and enantioselectivity are discussed. Interestingly, for the entropically driven separations, enantiomeric selectivity can increase at higher temperatures, even with decreasing retention.