336105-29-4

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 196929-78-9 (R)-2-methylpropane-2-sulfinamide 

Downstream Products

• 911372-72-0 (R_S)-N-((R)-1,3-diphenylpropyl)-2-methylpropane-2-sulfinamide 
• 847049-39-2 (R_S)-N-((S)-1,3-diphenylpropyl)-2-methylpropane-2-sulfinamide 
• 865355-08-4 2-Methyl-propane-2-sulfinic acid ((1S,2R)-2-hydroxy-3-methyl-1-phenethyl-butyl)-amide 
• 1021167-13-4 (R(S),2S,3S,1'R)-N-(tert-butylsulfinyl)-2-(1-amino-3-phenylpropyl)-3-ethylcyclohexanone 
• 1029700-77-3 (R)-2-methyl-N-((R)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)propane-2-sulfinamide 
• 1268240-88-5 (R)-N-((S)-1-(4-fluorophenyl)-4-phenylbutan-2-yl)-2-methylpropane-2-sulfinamide 

Relevant academic research and scientific papers

Crystal structures of reversible ketone-Based inhibitors of the cysteine protease cruzain

The crystal structures of two hydroxymethyl ketone inhibitors complexed to the cysteine protease cruzain have been determined at 1.1 and 1.2 A resolution, respectively. These high resolution crystal structures provide the first structures of non-covalent inhibitors bound to cruzain. A series of compounds were prepared and tested based upon the structures providing further insight into the key binding interactions.

IMMUNOPROTEASOME INHIBITORS

Provided herein are compounds, such as a compound of Formula (I), as described herein, or a pharmaceutically acceptable salt thereof, that are immunoproteasome (such as LMP2 and LMP7) inhibitors. The compounds described herein can be useful for the treatment of diseases treatable by inhibition of immunoproteasomes. Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

Stereoselective Coupling of N-tert-Butanesulfinyl Aldimines and β-Keto Acids: Access to β-Amino Ketones

The reaction of chiral N-tert-butanesulfinyl aldimines with β-keto acids under basic conditions at room temperature proceeds with high levels of diastereocontrol, leading to β-amino ketones in high yields. Based on DFT calculations, an eight-membered cyclic transition state involving coordination of the lithium atom to the oxygens of carboxylate and sulfinyl units was proposed, being in agreement with the observed experimental diastereomeric ratios. The synthesis of the piperidine alkaloid (-)-pelletierine was successfully undertaken in order to demonstrate the utility of this methodology.

Asymmetric synthesis of amines by the knochel-type MgCl2- enhanced addition of benzyl zinc reagents to N -tert -Butanesulfinyl aldimines

The MgCl2-enhanced addition of benzyl zinc reagents to N-tert-butanesulfinyl imines proceeds readily at room temperature to afford the N-tert-butanesulfinyl-protected amine products in good yields and diastereomeric ratios. This method is functional group tolerant in both the imine substrate and benzyl zinc coupling partner. Moreover, benzyl zinc reagent addition to the N-tert-butanesulfinyl imine 3o prepared from isopropylidene-protected glyceraldehyde proceeds in high yield and with exceptional selectivity to provide rapid entry to hydroxyethylamine-based aspartyl protease inhibitors.(Figure Presented)

Influence of HMPA on the stereochemical outcome of the addition of a racemic allenylzinc onto enantiopure N-terf-butanesulfinimines: Stereoselective access to enantiopure cis-ethynylaziridines

In the presence of 60 equivalents of HMPA, the condensation of the racemic allenylzinc derived from l -chloro-3-trimethylsilylpropyne onto enantiopure non-a-branched N-tert-butanesulfinimines was proven to give access to the corresponding cis-ethyny-lazir

Diastereoselective and enantioselective Rh(I)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines

Two new Rh(I)-catalyzed methods for the synthesis of chiral α-branched amines via addition of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl imines have been developed. The syntheses are more functional group tolerant than alternativ

Self-condensation of N-tert-butanesulfinyl aldimines: Application to the rapid asymmetric synthesis of biologically important amine-containing compounds

(Chemical Equation Presented) Highly diastereoselective intra- and intermolecular self-condensation reactions of N-tert-butanesulfinyl aldimines have been developed and applied to the rapid, asymmetric synthesis of frans-2-aminocyclopentanecarboxylic acid and the drug candidate SC-53116. Key to both syntheses is a novel microwave-assisted reaction in which N-sulfinyl aldimines are cleanly converted into nitrites in high-yielding concerted elimination processes.