1190958-35-0

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 343338-28-3 (S)-2-methylpropane-2-sulfinamide 

Downstream Products

• 1126903-68-1 (S(S),2S,3S,1'S)-N-(tert-butylsulfinyl)-2-(1-amino-3-phenylpropyl)-3-methylcyclohexanone 
• 1072804-68-2 (4S,S(S))-N-(tert-butylsulfinyl)-6-phenylhex-1-en-4-amine 
• 1211540-46-3 (R)-3-methylene-5-(2-phenylethyl)pyrrolidin-2-one 
• 1211540-40-7 (S)-3-methylene-5-(2-phenylethyl)pyrrolidin-2-one 
• 1412429-51-6 dimethyl [(1S)-1-{[(S)-(tert-butyl)sulfinyl]amino}-3-phenylpropyl]propanedioate 
• 1587692-02-1 (S,S_S)-N-(tert-butylsulfinyl)-1-nitro-4-phenylbutan-2-amine 
• 1587692-03-2 C₁₄H₂₂N₂O₃S 
• 1582803-11-9 (S)-N-((S)-5-fluoro-1-phenylhex-5-en-3-yl)-2-methylpropane-2-sulfinamide 

Relevant academic research and scientific papers

Stereoselective synthesis of 5-(1-aminoalkyl)-2-pyrrolidones and 1,7-diazaspiro[4.5]decane-2,8-diones from chiral N-tert-butanesulfinyl imines and ethyl 4-nitrobutanoate

The reaction of N-tert-butanesulfinyl imines with ethyl 4-nitrobutanoate under basic conditions produced nitro amine derivatives. The resulting β-nitroamine derivatives, isolated as a 1:1 mixture of epimers, were easily transformed into 5-(1-aminoalkyl)-2

Asymmetric [3+2] Annulation Approach to 3-Pyrrolines: Concise Total Syntheses of (-)-Supinidine, (-)-Isoretronecanol, and (+)-Elacomine

An asymmetric [3+2] annulation reaction to form 3-pyrroline products is reported. Upon treatment with lithium diisopropylamide, readily available ethyl 4-bromocrotonate is deprotonated and trapped with Ellman imines selectively at the α-position to yield enantiopure 3-pyrroline products. This new method is compatible with aryl, alkyl, and vinyl imines. The efficacy of the method is showcased by short asymmetric total syntheses of (-)-supinidine, (-)-isoretronecanol, and (+)-elacomine. This novel annulation approach also works for an aldehyde, thus providing access to a 2,5-dihydrofuran product in a single step from simple precursors. By modifying the structure of the carbanion nucleophile, an asymmetric vinylogous aza-Darzens reaction can be realized.

Investigating the phosphinic acid tripeptide mimetic DG013A as a tool compound inhibitor of the M1-aminopeptidase ERAP1

ERAP1 is a zinc-dependent M1-aminopeptidase that trims lipophilic amino acids from the N-terminus of peptides. Owing to its importance in the processing of antigens and regulation of the adaptive immune response, dysregulation of the highly polymorphic ERAP1 has been implicated in autoimmune disease and cancer. To test this hypothesis and establish the role of ERAP1 in these disease areas, high affinity, cell permeable and selective chemical probes are essential. DG013A 1, is a phosphinic acid tripeptide mimetic inhibitor with reported low nanomolar affinity for ERAP1. However, this chemotype is a privileged structure for binding to various metal-dependent peptidases and contains a highly charged phosphinic acid moiety, so it was unclear whether it would display the high selectivity and passive permeability required for a chemical probe. Therefore, we designed a new stereoselective route to synthesize a library of DG013A 1 analogues to determine the suitability of this compound as a cellular chemical probe to validate ERAP1 as a drug discovery target.

First sonochemical, simple and solvent-free synthesis of chiral tert-butanesulfinimines using silica supported p-toluenesulfonic acid

A solvent-free, versatile procedure has been developed for the effective synthesis of tert-butanesulfinylimines of a variety of aldehydes using chiral tert-butanesulfinamides under green, sonochemical conditions. This method utilizes silica supported p-to

Enantiodivergent Approach to the Synthesis of Cis-2,6-Disubstituted Piperidin-4-ones

Enantiopure β-amino ketone derivatives were synthesized by decarboxylative Mannich reaction of chiral N-tert-butanesulfinyl imines with β-keto acids and were subsequently transformed into cis-2,6-disubstituted piperidin-4-ones through an organocatalyzed condensation with aldehydes. Both enantiomers were accessible from the same precursors by inverting the order in the reaction sequence of the aldehydes involved in the imine formation and the intramolecular Mannich condensation. The synthesis of the piperidine alkaloids (+)-241D, (-)-epimyrtine, and (-)-lasubine II demonstrated the utility of this methodology.

Total Synthesis of K777: Successful Application of Transition-Metal-Catalyzed Alkyne Hydrothiolation toward the Modular Synthesis of a Potent Cysteine Protease Inhibitor

We report the total synthesis of K777 and a series of analogues via alkyne hydrothiolation catalyzed by Wilkinson's complex (ClRh(PPh3)3). The alkyne hydrothiolation reactions proceeded with excellent regio- and diastereoselectivity

Base-promoted diastereoselective addition of nitromethane and nitroethane to N-tert-butylsulfinyl imines: Synthesis of N-protected α-amino acids and amino ketones

The reaction of N-tert-butylsulfinyl imines with nitromethane or nitroethane in the presence of NaHCO3 under solvent-free reaction conditions gave β-nitro amine derivatives with reasonable levels of diastereoselectivity. Enantioenriched N-tert-

Exploration of cathepsin S inhibitors characterized by a triazole P1-P2 amide replacement

This paper details exploration of a class of triazole-based cathepsin S inhibitors originally reported by Ellman and co-workers. SAR studies involving modifications across the whole inhibitor provide a perspective on the strengths and weaknesses of this class of inhibitors. In addition, we put the unique characteristics of this class of compounds into perspective with other classes of cathepsin S inhibitors.

Modular stereoeontrolled assembly of R2Zn, cyclic enones and N-tert-butanesulfinyl imines

The assembly of a wide range of dialkylzincs, cyclic enones, and chiral N-tert-butylsulfinyl imines in the presence of the appropriate phosphoramidite ligands allowed the formation of β-amino ketones with three consecutive stereogenic centers in a stereoc