159155-12-1

Usage

Uses

Used in Organic Synthesis:
(S)-methyl 3-hydroxy-2-(2,4,6-triisopropylphenylsulfonamido)propanoate is used as a reagent in organic synthesis for the preparation of various biologically active molecules. Its unique structure and functional groups make it a valuable building block in the creation of complex organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (S)-methyl 3-hydroxy-2-(2,4,6-triisopropylphenylsulfonamido)propanoate is used as a potential drug candidate due to its pharmacological properties. Its chiral nature also makes it a promising candidate for the development of chiral catalysts and asymmetric synthesis methods, which are essential in the production of enantiomerically pure drugs.
Used in Chiral Catalyst Development:
(S)-methyl 3-hydroxy-2-(2,4,6-triisopropylphenylsulfonamido)propanoate's chiral center allows it to be used in the development of chiral catalysts, which are crucial for the synthesis of enantiomerically pure compounds. This application is particularly important in the pharmaceutical industry, where the desired biological activity is often associated with a specific enantiomer.
Used in Asymmetric Synthesis Methods:
(S)-methyl 3-hydroxy-2-(2,4,6-triisopropylphenylsulfonamido)propanoate is also utilized in asymmetric synthesis methods, which are vital for producing optically active compounds with a single enantiomer. This is particularly relevant in the synthesis of pharmaceuticals, where the desired therapeutic effect is often enantioselective.

Upstream product

• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 2788-84-3 (S)-serine methyl ester 

Downstream Products

• 1352790-94-3 (R)-(2,2-dimethyl-3-((2,4,6-triisopropylphenyl)sulfonyl)-1,3-oxazolidin-4-yl)methanol 
• 1352790-95-4 (S)-2,2-dimethyl-3-((2,4,6-triisopropylphenyl)sulfonyl)-1,3-oxazolidine-4-carbaldehyde 
• 1352790-96-5 (R,Z)-N-((2,2-dimethyl-3-((2,4,6-triisopropylphenyl)sulfonyl)-1,3-oxazolidin-4-yl)methylene)aniline oxide 
• 1352790-93-2 (S)-methyl 2,2-dimethyl-3-((2,4,6-triisopropylphenyl)sulfonyl)-1,3-oxazolidine-4-carboxylate 

Relevant academic research and scientific papers

Discovery of O-(3-carbamimidoylphenyl)-l-serine amides as matriptase inhibitors using a fragment-linking approach

Matriptase is a cell-surface trypsin-like serine protease of epithelial origin, which cleaves and activates proteins including hepatocyte growth factor/scatter factor and proteases such as uPA, which are involved in the progression of various cancers. Here we report a fragment-linking approach, which led to the discovery of O-(3-carbamimidoylphenyl)-l-serine amides as potent matriptase inhibitors. The co-crystal structure of one of the potent inhibitors, 6 in complex with matriptase catalytic domain validated the working hypothesis guiding the development of this congeneric series and revealed the structural basis for matriptase inhibition. Replacement of a naphthyl group in 6 with 2,4,6-tri-isopropyl phenyl resulted in 10 with improved matriptase inhibition, which exhibited significant primary tumor growth inhibition in a mouse model of prostate cancer. Compounds such as 10, identified using a fragment-linking approach, can be explored further to understand the role of matriptase as a drug target in cancer and inflammation.

An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations

The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.

Asymmetric pericyclic cascade approach to spirocyclic oxindoles

The reaction of chiral N-arylnitrones with carbocyclic alkylarylketenes generates spirocyclic oxindoles in good yields and with excellent levels of enantioselectivity (90-99% ee) via a pericyclic cascade process.

Pericyclic cascade with chirality transfer: Reaction pathway and origin of enantioselectivity of the hetero-claisen approach to oxindoles

A new pericyclic cascade is proposed for the chiral auxiliary-controlled synthesis of 3,3-disubstituted oxindoles from nitrones and ketenes. The remarkable acyclic 1,6-stereochemical induction, hitherto unexplained, is rationalized by a stereoselective 3+