137365-16-3

Usage

Uses

Used in Chemical Synthesis:
(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL is used as a reagent for the highly enantioselective addition of primary alkyl Grignards to ketones. This application is significant in the synthesis of chiral compounds, which are essential in the pharmaceutical industry for the development of drugs with specific biological activities.
Used in Asymmetric Catalysis:
In the field of asymmetric catalysis, (+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL serves as a chiral auxiliary for the asymmetric addition of nucleophiles to carbonyls. This role is crucial in creating enantiomerically pure compounds, which are important for the development of drugs with fewer side effects and improved efficacy.
Used in Pharmaceutical Industry:
(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and chiral properties make it a valuable building block for the development of new drugs with improved therapeutic profiles.
Used in Research and Development:
In the research and development sector, (+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL is utilized as a tool to study the effects of chirality on molecular interactions and biological activities. This knowledge can be applied to design more effective and selective drugs, as well as to understand the underlying mechanisms of various biological processes.
Used in Analytical Chemistry:
(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL can be employed as a chiral reference standard in analytical chemistry. It helps in the identification and quantification of enantiomers in various samples, which is important for quality control and ensuring the purity of chiral compounds in the pharmaceutical and chemical industries.

InChI:InChI=1/C47H38O4/c1-45(2)50-43(46(48,39-23-19-31-11-3-7-15-35(31)27-39)40-24-20-32-12-4-8-16-36(32)28-40)44(51-45)47(49,41-25-21-33-13-5-9-17-37(33)29-41)42-26-22-34-14-6-10-18-38(34)30-42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m0/s1

Upstream product

• 580-13-2 2-bromonaphthalene 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 1236286-39-7 C₁₄H₁₆N₂*C₄₇H₃₈O₄ 
• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 

Downstream Products

• 1236286-39-7 C₁₄H₁₆N₂*C₄₇H₃₈O₄ 

Relevant academic research and scientific papers

Phosphite-Catalyzed C?H Allylation of Azaarenes via an Enantioselective [2,3]-Aza-Wittig Rearrangement

A phosphite-mediated [2,3]-aza-Wittig rearrangement has been developed for the regio- and enantioselective allylic alkylation of six-membered heteroaromatic compounds (azaarenes). The nucleophilic phosphite adducts of N-allyl salts undergo a stereoselective base-mediated aza-Wittig rearrangement and dissociation of the chiral phosphite for overall C?H functionalization of azaarenes. This method provides efficient access to tertiary and quaternary chiral centers in isoquinoline, quinoline, and pyridine systems, tolerating a broad variety of substituents on both the allyl part and azaarenes. Catalysis with chiral phosphites is also demonstrated with synthetically useful yields and enantioselectivities.

Preparation method of chiral catalyst ligand TADDOLs in asymmetric synthesis

The invention discloses a preparation method of a chiral catalyst ligand TADDOLs in asymmetric synthesis. The preparation method comprises the following steps of using chiral diethyl tartrate as raw material, and reacting with 2,2-dimethoxypropane and triethyl orthoformate, so as to obtain O,O-isopropylidene diethyl tartrate; enabling brominated aromatic hydrocarbon and isopropyl magnesium bromideto react in a solvent; finally, adding the O,O-isopropylidene diethyl tartrate, so as to obtain a target product, namely the chiral catalyst ligand TADDOLs. The preparation method has the advantagesthat the raw materials are bulk chemicals, the industrial cost is low, the reaction process is moderate and controllable, the post-treatment is concise and efficient, the difficulty in industrial production of the series of compound is decreased, and the cost is reduced; the chiral catalyst ligand TADDOLs has been widely applied into the asymmetric chiral synthesis; especially, when the chiral catalyst ligand TADDOLs and metal form a complex as the catalyst in the chiral oriented synthesis, the effect is obvious; the catalyzing effect is excellent, the process of chiral detachment of despinner compound is reduced, and the synthesis cost of chiral medicine is reduced.

Enantioselective Ni-Al Bimetallic Catalyzed exo -Selective C-H Cyclization of Imidazoles with Alkenes

A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.

Ni-Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne

A Ni-Al bimetallic catalyzed enantioselective cycloaddition reaction of cyclopropyl carboxamides with alkynes has been developed. A series of cyclopentenyl carboxamides were obtained in up to 99% yield and 94% ee. The bifunctional-ligand-enabled bimetallic catalysis proved to be an efficient strategy for the C-C bond cleavage of unreactive cyclopropanes.

A quaternary phosphonium salt compound and its preparation method

The present invention discloses a quaternary phosphonium salt compound and a preparation method thereof. The method uses cheap and readily available L-tartaric acid as the raw material, and conducts carboxyl esterification, hydroxyl protection, Grignard reaction, azide substitution, azide reduction and final reaction with phosphorus pentachloride, so as to obtain the quaternary phosphonium salt compound. The quaternary phosphonium salt compound is a novel Bronsted acid catalyst (a hydrogen bond donor catalyst), and can be used in the catalysis of asymmetric Mannich reaction, Michael reaction and Henry reaction.

Easily accessible TADDOL-derived bisphosphonite ligands: Synthesis and application in the asymmetric hydroformylation of vinylarenes

The synthesis of chiral bidentate bisphosphonite ligands based on the TADDOL motif from readily available starting materials has been developed. Taking advantage of the modular nature of the building blocks, a diverse ligand library has been prepared. Their catalytic potential has been evaluated in the asymmetric hydroformylation of styrene and derivatives. These catalysts showed high activity and provided the aldehydes in high enantiomeric purity.

Optical monitoring of gases with cholesteric liquid crystals

A new approach to optical monitors for gases is introduced using cholesteric liquid crystals doped with reactive chiral compounds. The approach is based on cholesteric pitch length changes caused by a change in helical twisting power (HTP) of the chiral dopants upon reaction with the analyte. The concept is demonstrated for monitoring carbon dioxide via reversible carbamate formation and for oxygen using the irreversible oxidation of a chiral dithiol to a disulfide. Monitoring of CO2 was achieved by doping a commercial cholesteric liquid crystalline mixture (E7) with 1.6% mol of the 1:1 complex of an optically pure diamine with a TADDOL derivative. Upon exposure to carbon dioxide, the reflection band of a thin film of the mixture shifted from 637 to 495 nm as a consequence of dissociation of the complex after carbamate formation of the diamine. An O2 monitor was obtained by doping E7 with a chiral binaphthyl dithiol derivative and a nonresponsive codopant. The reflection band of the oxygen monitor film changed from 542 to 600 nm, due to the conformational change accompanying oxidation of the dithiol to disulfide. These monitoring mechanisms hold promise for application In smart packaging, where carbon dioxide and oxygen are of special interest because of their roles in food preservation.

Enantioselective catalysis of the hetero-diels-alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation: A one-step synthesis of (S)-(+)-dihydrokawain

The first catalytic enantioselective hetero-Diels-Alder reaction between Brassard's diene and aldehydes has been achieved through hydrogen-bonding activation using TADDOL derivatives as catalysts to afford the corresponding δ-lactone derivatives in modera