111293-23-3

Usage

Uses

Used in Pharmaceutical Research and Development:
(-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE is used as a chiral building block for the development of new pharmaceutical compounds. Its unique stereochemistry allows for the creation of enantiomerically pure drugs, which can have different biological activities and reduce potential side effects.
Used in Organic Synthesis:
In the field of organic synthesis, (-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE serves as an important intermediate for the synthesis of various organic compounds. Its reactivity and ethoxycarbonyl ethyl groups make it a valuable component in the construction of complex molecular structures.
Used in the Production of Fine Chemicals:
(-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE is utilized in the production of fine chemicals, which are high-purity chemicals used in various industries such as pharmaceuticals, agriculture, and materials science. Its versatility and reactivity contribute to the synthesis of these high-quality specialty chemicals.
Used in the Production of Pharmaceutical Intermediates:
(-)-BIS[(S)-1-(ETHOXYCARBONYL)ETHYL] FUMARATE is also used in the production of pharmaceutical intermediates, which are essential building blocks in the synthesis of final drug products. Its role in creating these intermediates is crucial for the development and manufacturing of various medications.

InChI:InChI=1/C14H20O8/c1-5-19-13(17)9(3)21-11(15)7-8-12(16)22-10(4)14(18)20-6-2/h7-10H,5-6H2,1-4H3/b8-7+/t9-,10-/m0/s1

Upstream product

• 687-47-8 (S)-Ethyl lactate 
• 627-63-4 fumaryl dichloride 
• 108-31-6 maleic anhydride 
• 97-64-3 ethyl 2-hydroxypropionate 

Downstream Products

• 111293-21-1 (1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid bis-((S)-1-ethoxycarbonyl-ethyl) ester 
• 111293-20-0 (1R,2R)-Cyclohex-4-ene-1,2-dicarboxylic acid bis-((S)-1-ethoxycarbonyl-ethyl) ester 
• 142608-04-6 (1R,3R,4S)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (S)-1-ethoxycarbonyl-ethyl ester 
• 142696-88-6 (1S,3S,4R)-2-(Toluene-4-sulfonyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (S)-1-ethoxycarbonyl-ethyl ester 
• 142608-03-5 (S)-2-{2-[(E)-Toluene-4-sulfonylimino]-acetoxy}-propionic acid ethyl ester 

Relevant academic research and scientific papers

Simple and highly efficient chiral dopant molecules possessing both rod- and arch-like units

A simple chiral dopant molecule (R)-1 with both rod- and arch-like units was prepared, and extremely large helical twisting powers (+123 to +228 μm-1) in nematic liquid crystal phases were achieved. We have demonstrated that the introduction of an arch-like unit in addition to rod-like units is highly effective in controlling the helical molecular alignment. As an application of the dopant, induction of blue phases by addition of a small amount of it was achieved. This journal is the Partner Organisations 2014.

The aza-Diels-Alder reaction protocol - A useful approach to chiral, sterically constrained α-amino acid derivatives

Different types of polycyclic α-amino acid derivatives are prepared from chiral imines by using well-established aza-Diels-Alder reaction conditions. Simply by varying the diene moiety, different products such as spirocyclic compounds 8 and 9, anthracene 10, and tetrahydroquinolines 15-21 are formed.

Enantioselective synthesis of dual 5-HT4/5-HT3 serotonergic azanoradamantane SC-52491

A racemic synthesis of azanoradamantane (±)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e.