455333-80-9

Upstream product

• 106-95-6 allyl bromide 
• 329912-92-7 (2S)-methyl 2-(4-nitrobenzenesulfonamido)propanoate 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Downstream Products

• 884494-29-5 (S)-2-[Allyl-(4-nitro-benzenesulfonyl)-amino]-propionyl fluoride 
• 884494-28-4 (S)-2-[Allyl-(4-nitro-benzenesulfonyl)-amino]-propionyl chloride 
• 1613295-40-1 (S)-N-allyl-N-(1-hydroxypropan-2-yl)-4-nitro-benzenesulfonamide 
• 1613295-37-6 (3aS,6S,6aS)-6-methyl-5-[(4-nitrophenyl)sulfonyl]-3,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole 
• 1613295-38-7 (3aS,6S,6aR)-6-methyl-5-[(4-nitrophenyl)sulfonyl]-3,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole 
• 1613295-39-8 C₁₂H₁₄N₂O₄S 
• 884494-19-3 (S)-2-[allyl(4-nitrobenzenesulfonyl)amino]propionic acid 

Relevant academic research and scientific papers

Tosylhydrazide-Promoted Diastereoselective Intramolecular 1,3-Dipolar Cycloadditions: Synthesis of Tetrahydropyrrolo[3,4-c]pyrazoles

A very straightforward diastereoselective synthesis of tetrahydropyrrolo[3,4-c]pyrazoles by intramolecular 1,3-dipolar cycloaddition is described. The starting materials for the synthetic route are N-Boc-protected α-amino acids, which are first transformed into N-allyl-α-amino ketones through conventional methodologies. Then, a one-pot sequence that involves formation of a tosylhydrazone from the ketone, base-induced decomposition of the hydrazone, and intramolecular 1,3-dipolar cycloaddition of the diazo compound generated, gives rise to the bicyclic systems with total diastereoselectivity and high preservation of the enantiomeric purity. However, the analogous process employing α-amino aldehydes lacks stereoselectivity. DFT computational modeling has been carried out to account for the different behavior of the two types of systems.

Tosylhydrazide-promoted diastereoselective intramolecular 1,3-dipolar cycloadditions: Synthesis of tetrahydropyrrolo[3,4-c]pyrazoles

A very straightforward diastereoselective synthesis of tetrahydropyrrolo[3, 4-c]pyrazoles by intramolecular 1,3-dipolar cycloaddition is described. The starting materials for the synthetic route are N-Boc-protected α-amino acids, which are first transformed into N-allyl-α-amino ketones through conventional methodologies. Then, a one-pot sequence that involves formation of a tosylhydrazone from the ketone, base-induced decomposition of the hydrazone, and intramolecular 1,3-dipolar cycloaddition of the diazo compound generated, gives rise to the bicyclic systems with total diastereoselectivity and high preservation of the enantiomeric purity. However, the analogous process employing α-amino aldehydes lacks stereoselectivity. DFT computational modeling has been carried out to account for the different behavior of the two types of systems. Copyright

3,5-Bis(n-perfluorooctyl)benzyltriethylammonium bromide (F-TEBA): An efficient, easily recoverable fluorous catalyst for solid-liquid PTC reactions

A readily available 3,5-bis(perfluorooctyl)benzyl bromide and triethylamine were reacted under mild conditions to give 3,5-bis(n-perfluorooctyl) benzyltriethylammonium bromide (F-TEBA), an analogue of the versatile phase-transfer catalyst, benzyltriethyla

Macrocyclic peptidomimetic inhibitors of β-secretase (BACE): First X-ray structure of a macrocyclic peptidomimetic-BACE complex

The synthesis of novel macrocyclic peptidomimetic inhibitors of the enzyme BACE1 is described. These macrocycles are derived from a hydroxyethylene core structure. Compound 7 was co-crystallized with BACE1 and the X-ray structure of the complex elucidated at 1.6 A resolution. This molecule inhibits the production of the Aβ peptide in HEK293 cells overexpressing APP751sw.

Novel observation concerning the nitrobenzenesulfonamide protecting group

In an ongoing work directed towards the synthesis of nucleoside derivatives containing an l-alanine residue, we report herein a novel observation concerning the Ns-protecting group: the epimerization of the α-hydrogen in acylation conditions.

A general approach to dehydro-Freidinger lactams: Ex-chiral pool synthesis and spectroscopic evaluation as potential reverse turn inducers

Starting from natural α-amino acids, a practical synthesis of the dehydro-Freidinger lactams 9a-h based on the ring-closing olefin metathesis reaction was investigated. The presented examples comprise 6-, 7-, 8-, 9-, and 10-membered cyclic dipeptide mimics. Structural variations were demonstrated. We approached the metathesis precursors 8a-h employing an N-alkylation/peptide-coupling strategy. Subsequent ring closure was promoted by the ruthenium-based catalyst 10a or 10b. The resulting tetraresidue 11d was shown to undergo intramolecular hydrogen bonding based on NMR and FT-IR studies. Thus, the development of dehydro-Freidinger lactams as potential reverse turn inducers stabilizing an intramolecular NHi+3...COi hydrogen-bond was demonstrated.

Short and efficient synthesis of Homo-Freidinger lactams: An olefin metathesis approach towards conformationally restricted β-amino acid analogues

Peptide coupling of the N-allyl or N-homoallyl α-amino acid esters 6a-d with enantiomerically pure β-C-allylglycine gave access to the dienes 7a-d which were subjected to an olefin metathesis reaction. Thus, the novel lactam bridged peptide mimics 8a-d we