1357471-22-7

Upstream product

• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 259212-61-8 (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 1357471-25-0 trans-4-tert-butyldiphenylsiloxy-N-Boc-L-proline benzyl ester 

Downstream Products

• 1357471-23-8 1,6-di(trans-N-Boc-4-tert-butlydiphenylsiloxy-L-prolinamide)hexane 
• 1357471-24-9 1,6-di(trans-4-tertbutlydiphenylsiloxy-L-prolinamide)hexane 
• 1431160-02-9 di-tert-butyl 5,5′-(5,8-dioxa-2,11-diazadodecane-1,12-dioyl)-bis(3-((tert-butyldiphenylsilyl)oxy)pyrrolidine-1-carboxylate) 
• 1431160-03-0 N,N′-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-((tertbutyldiphenylsilyl)oxy)pyrrolidine-2-carboxamide) 

Relevant academic research and scientific papers

Synergistic effects within a C2-symmetric organocatalyst: The potential formation of a chiral catalytic pocket

This study describes the synthesis of five novel C2-symmetric organocatalysts that facilitate the on-water asymmetric aldol reaction at low catalyst loading (1 mol%) without the use of additives. Each catalyst is composed of two diprolinamide units joined by a symmetric alkyl bridging group allowing for systematic modulation of catalytic site proximity. Typically, catalysts in this manuscript which bear the catalytic units in close proximity gave the best reaction outcomes in terms of conversion (up to >99%), diastereomeric ratio (4/96, syn/anti) and enantiomeric excess (up to 97%). This effect has been attributed to the assembly of a chiral pocket, facilitated by hydrogen bonding at the oil-in-water interface. The Royal Society of Chemistry 2013.

IONIZABLE COMPOUNDS AND COMPOSITIONS AND USES THEREOF

This invention includes ionizable compounds, and compositions and methods of use thereof. The ionizable compounds can be used for making nanoparticle compositions for use in biopharmaceuticals and therapeutics. More particularly, this invention relates to compounds, compositions and methods for providing nanoparticles to encapsulate active agents, such as nucleic acid agents, and to deliver and distribute the active agents to cells, tissues, organs, and subjects.

Direct asymmetric aldol reactions in water catalysed by a highly active C2-symmetrical bisprolinamide organocatalyst

A novel C2-symmetrical bisprolinamide organocatalyst was synthesised and used to facilitate asymmetric direct aldol reactions in a water emulsion. Reactions were performed at room temperature with very low catalyst loadings (1-2.5 mol%) without the required use of additives, co-catalysts or extended reaction times (24 h). This catalyst system was then used with a variety of aldehyde substrates showing good reaction generality for benzaldehydes with cyclohexanone (dr range 77/23 to 99/1, anti/syn; ee range 33% to 99%) and moderate scope with cyclopentanone (dr range 45/55 to 76/24, anti/syn; ee range 14% to 68%). Ultra-low catalysts loadings (0.1 and 0.05 mol%) were also investigated demonstrating catalyst turnover numbers in the order of 1000.