17136-46-8

Upstream product

• 2104-89-4 Ser-OMe 
• 98-59-9 p-toluenesulfonyl chloride 
• 2104-89-4 D-serine methyl ester 
• 5874-57-7 R-(-)-serine methyl ester hydrochloride 
• 67-56-1 methanol 
• 5873-13-2 (R)-2-(p-Tolylsulfonamido)serine 
• 56-45-1 L-serin 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 5873-11-0 3-hydroxy-2-{(4-methylphenyl)sulphonamino}propanoic acid 

Downstream Products

• 141662-71-7 O-(3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-β-D-lyxo-hexopyranosyl)-N-tosyl-L-serine methyl ester 
• 141662-72-8 O-(3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-α-D-lyxo-hexapyranosyl)-N-tosyl-L-serine methyl ester 
• 128154-34-7 N-Tosyl-O-(2,3,4-tri-O-acetyl-β-D-arabinopyranosyl)-L-serine methyl ester 
• 129188-73-4 N-tosyl-O-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)-L-serine methylester 
• 105424-75-7 methyl (2S)-1-[(4-methylphenyl)sulfonyl]aziridine-2-carboxylate 
• 188816-51-5 (S)-2-(Toluene-4-sulfonylamino)-3-trityloxy-propionic acid methyl ester 
• 209266-09-1 methyl (S)-3-tret-butyldimethylsilyloxy-2-(4-methylphenylsulfamido)propanoate 
• 219851-87-3 N-(4-toluenesulfonyl)-N-(tert-butoxycarbonyl)-α,β-didehydroalanine methylester 
• 128154-29-0 O-(3,4-di-O-acetyl-2-deoxy-2-hydroxyimino-β-D-erythro-pentopyranosyl)-N-tosyl-L-serine methylester 
• 128154-28-9 O-(3,4-di-O-acetyl-2-deoxy-2-hydroxyimino-α-D-erythro-pentopyranosyl)-N-tosyl-L-serine methylester 

Relevant academic research and scientific papers

The formal synthesis of lucentamycin A: Construction of cis-2,3-disubstituted pyrrolidine core by application of SmI2-DMPU system

The formal synthesis of lucentamycin A (1) was accomplished in 14 steps from D-serine methyl ester as a starting material. All the requisite stereogenic centers on the pyrrolidine core of 1 were controlled by SmI2-mediated cyclization. Construc

Cu-Catalyzed [3 + 3] Cycloaddition of Isocyanoacetates with Aziridines and Stereoselective Access to α,γ-Diamino Acids

We report herein an efficient Cu-catalyzed formal [3 + 3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyrimidine derivatives. In pa

A formal synthesis of (–)-kainic acid by means of SMI2-mediated radical cyclization

A formal synthesis of (–)-kainic acid (1) starting from the known D-serine derivative 9 has been established in 14 steps. Construction of all the stereogenic centers on the pyrrolidine core of 1 was successfully achieved by application of SmI2-mediated radical cyclization to the α,β-unsaturated ester having an alkyne moiety, followed by hydroxy group directed diastereoselective hydrogenation over Wilkinson’s catalyst.

Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy

Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.

Two rearrangement pathways in the geminal acylation of 2-methoxyoxazolidines leading to substituted 1,4-oxazines

Lewis acid-mediated geminal acylation of 2-methoxyoxazolidines with five- or six-membered acyloins followed by heterocyclization afforded 1,4-oxazines fused to cyclopentenone or cyclohexenone rings. Overall yields ranged from 30 to 73%. The position of the carbonyl group in the products depended on whether or not water was present during the ringexpanding acyl migration step. The route lacking water during the acyl migration step was best conducted in one pot. The addition of water effected cleavage of a silyloxy group in the intermediate during the initial Mukaiyama aldol reaction prior to the acyl migration.

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.

Novel sulfonamide TRPA1 receptor antagonists

The invention discloses compounds of Formula I The compounds of formula I are TRPA1 antagonists and are useful as active ingredients of pharmaceutical compositions for the treatment of pain and other conditions ameliorated by the inhibition of TRPA1 receptors.

NOVEL SULFONAMIDE TRPA1 RECEPTOR ANTAGONISTS

The invention discloses compounds of Formula (I). The compounds of formula (I) are TRPA1 antagonists and are useful as active ingredients of pharmaceutical compositions for the treatment of pain and other conditions ameliorated by the inhibition of TRPA1 receptors.

Discovery of cell-permeable inhibitors that target the BRCT domain of BRCA1 protein by using a small-molecule microarray

BRCTs are phosphoserine-binding domains found in proteins involved in DNA repair, DNA damage response and cell cycle regulation. BRCA1 is a BRCT domain-containing, tumor-suppressing protein expressed in the cells of breast and other human tissues. Mutations in BRCA1 have been found in ca. 50% of hereditary breast cancers. Cell-permeable, small-molecule BRCA1 inhibitors are promising anticancer agents, but are not available currently. Herein, with the assist of microarray-based platforms, we have discovered the first cell-permeable protein-protein interaction (PPI) inhibitors against BRCA1. By targeting the (BRCT)2 domain, we showed compound 15a and its prodrug 15b inhibited BRCA1 activities in tumor cells, sensitized these cells to ionizing radiation-induced apoptosis, and showed synergistic inhibitory effect when used in combination with Olaparib (a small-molecule inhibitor of poly-ADP-ribose polymerase) and Etoposide (a small-molecule inhibitor of topoisomerase II). Unlike previously reported peptide-based PPI inhibitors of BRCA1, our compounds are small-molecule-like and could be directly administered to tumor cells, thus making them useful for future studies of BRCA1/PARP-related pathways in DNA damage and repair response, and in cancer therapy.

Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion

An anti-Markovnikov geminal oxyamination of styrenyl alkenes in an intermolecular fashion using the umpolung strategy mediated by the bromonium ion is reported. Isotope labeling studies confirm the migration of the phenyl group in the semipinacol rearrang