118656-45-4

Upstream product

• 108-98-5 thiophenol 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 882-33-7 diphenyldisulfane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 

Downstream Products

• 106865-52-5 (S)-(+)-2-[(phenylthio)methyl]pyrrolidine 
• 192133-31-6 (S)-2-Benzenesulfonylmethyl-1-methyl-pyrrolidine 
• 118656-58-9 (1R,7aS)-1-Phenylsulfanyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 

Relevant academic research and scientific papers

(2 S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-catalyzed efficient stereoselective michael addition of cyclohexanone and cyclopentanone to nitroolefins

(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine, derived from l-proline, has been demonstrated as an efficient organocatalyst for the asymmetric Michael addition of cyclohexanone and cyclopentanone to β-nitrostyrenes. This pyrrolidine-based catalyst bearing a sulfoxide moiety was used to synthesize various γ-nitro carbonyl compounds in high yield (up to 97%) with excellent stereoselectivity (up to >99:1 dr and >99% ee) without the use of any additive.

Potent and selective nonpeptide inhibitors of caspases 3 and 7

5-Dialkylaminosulfonylisatins have been identified as potent, nonpeptide inhibitors of caspases 3 and 7. The most active compound within this series (34) inhibited caspases 3 and 7 in the 2-6 nM range and exhibited approximately 1000-fold selectivity for caspases 3 and 7 versus a panel of five other caspases (1, 2, 4, 6, and 8) and was at least 20-fold more selective versus caspase 9. Sequence alignments of the active site residues of the caspases strongly suggest that the basis of this selectivity is due to binding in the S2 subsite comprised of residues Tyr204, Trp206, and Phe256 which are unique to caspases 3 and 7. These compounds inhibit apoptosis in three cell-based models: human Jurkat T cells, human chondrocytes, and mouse bone marrow neutrophils.

Applications of organosulfur chemistry to organic synthesis: Total synthesis of (+)-himbeline and (+)-himbacine

Total syntheses of (+)-himbacine (1) and (+)-himbeline (2) are described. The synthesis involves the preparation of sulfone 38 and aldehyde 42 as single enantiomers followed by coupling of these compounds using a Julia-Lythgoe olefination. The preparation of sulfone 38 features an acid- promoted intramolecular Diels-Alder reaction of an α,β-unsaturated thioester while the synthesis of 42 features a Beak alkylation of piperidine 39.

Synthesis of chiral β-amino sulfides and β-amino thiols from α-amino acids

Bifurcated routes to two series of chiral secondary β-amino sulfides 5a-c and 11a-c have been developed from L-proline and (S)-phenylglycine, respectively. The developed methodology had also led to the synthesis of the tertiary β-amino thiol 7 and the primary β-amino sulfide 12 from L-proline and (S)-phenylglycine, respectively.