1035797-56-8

Upstream product

• 3282-30-2 pivaloyl chloride 
• 501-52-0 3-Phenylpropionic acid 
• 104-53-0 3-phenyl-propionaldehyde 
• 75-98-9 Trimethylacetic acid 

Downstream Products

• 136159-65-4 (R)-4-benzyl-3-(3-phenyl-propionyl)-oxazolidin-2-one 
• 1330117-35-5 (4R)-4-benzyl-3-((2S)-2-hydroxymethyl-3-phenylpropionyl)oxazolidin-2-one 
• 1330117-36-6 (4R)-4-benzyl-3-[(2S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-phenylpropionyl]oxazolidin-2-one 
• 1330117-37-7 (2S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-phenylpropionic acid 
• 1330117-38-8 (2R)-2-(tert-butyldiphenylsilanyloxymethyl)-3-phenylpropan-1-ol 
• 1330117-18-4 (2S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-phenylpropionaldehyde 
• 1330117-20-8 C₃₀H₃₄F₃NO₂Si 
• 10264-10-5 N-benzyl-3-phenylpropanamide 
• 21924-11-8 1-(3-phenylpropanoyl)piperidine 
• 170646-96-5 N-methoxy-N-methyl-3-phenylpropionamide 
• 704879-67-4 benzyl N-[(4S,5R)-4-benzyl-3-(3-phenylpropionyl)-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carboxylate 
• 93780-03-1 (S)-2-phenylmethylpent-4-enoic acid 
• 851968-91-7 benzyl N-[(4S,5S)-4-benzyl-3-(3-phenylpropionyl)-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carboxylate 
• 136159-65-4 (S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one 

Relevant academic research and scientific papers

Diastereoselective Aza-Mislow–Evans Rearrangement of N-Acyl tert-Butanesulfinamides into α-Sulfenyloxy Carboxamides

A diastereoselective [2,3] rearrangement of O-silyl N-sulfinyl N,O-ketene acetals derived from chiral N-acyl tert-butanesulfinamides was developed, giving α-sulfenyloxy carboxamides with excellent enantioselectivity. Enolization and subsequent silylation of N-acyl tert-butanesulfinamides initiate this aza variant of the Mislow–Evans rearrangement, in which the chirality at the sulfur atom in the rearrangement precursors is faithfully transferred to the α-carbon stereocenter of the products. The Ellman sulfinamide, often used as a chiral ammonia equivalent, can serve in this rearrangement as a chiral precursor for the asymmetric synthesis of α-oxygen-functionalized carboxamides.

Organocatalytic oxidation of aldehydes to mixed anhydrides

TEMPO catalyzes the direct oxidation of aldehydes to mixed anhydrides in the presence of a carboxylic acid. The anhydrides can be converted in situ to esters, secondary, tertiary or Weinreb amides in high yield. Oxidation of the aldehyde directly to 2-propyl esters is also possible using only catalytic amounts of acid. The oxidation reactions are rapid and take place under mild conditions.

(E)-alkene and ethylene isosteres substantially alter the hydrogen-bonding network in class II MHC Aq/glycopeptide complexes and affect T-cell recognition

The structural basis for antigen presentation by class II major histocompatibility complex (MHC) proteins to CD4+ T-cells is important for understanding and possibly treating autoimmune diseases. In the work described in this paper, (E)-alkene and ethylene amide-bond isosteres were used to investigate the effect of removing hydrogen-bonding possibilities from the CII259-270 glycopeptide, which is bound by the arthritis-associated murine Aq class II MHC protein. The isostere-modified glycopeptides showed varying and unexpectedly large losses of Aq binding that could be linked to the dynamics of the system. Molecular dynamics (MD) simulations revealed that the backbone of CII259-270 and the Aq protein are able to form up to 11 hydrogen bonds, but fewer than this number are present at any one time. Most of the strong hydrogen-bond interactions were formed by the N-terminal part of the glycopeptide, i.e., in the region where the isosteric replacements were made. The structural dynamics also revealed that hydrogen bonds were strongly coupled to each other; the loss of one hydrogen-bond interaction had a profound effect on the entire hydrogen-bonding network. The Aq binding data revealed that an ethylene isostere glycopeptide unexpectedly bound more strongly to Aq than the corresponding (E)-alkene, which is in contrast to the trend observed for the other isosteres. Analysis of the MD trajectories revealed that the complex conformation of this ethylene isostere was structurally different and had an altered molecular interaction pattern compared to the other Aq/glycopeptide complexes. The introduced amide-bond isosteres also affected the interactions of the glycopeptide/Aq complexes with T-cell receptors. The dynamic variation of the patterns and strengths of the hydrogen-bond interactions in the class II MHC system is of critical importance for the class II MHC/peptide/TCR signaling system.

Design and synthesis of a new polymer-supported Evans-type oxazolidinone: An efficient chiral auxiliary in the solid-ph ase asymmetric alkylation reactions

Wang resin-supported Evans' chiral auxiliary (23) was designed based on a novel polymer-anchoring strategy, which utilizes the 5-position of the oxazolidinone ring, and its new synthetic route applicable to multi-gram preparation in just a day was developed. Solid-phase Evans' asymmetric alkylation on 23-derived N-acylimide resin and following lithium hydroperoxide-mediated chemoselective hydrolysis afforded the corresponding α-branched carboxylic acids in desired high stereoselectivities (up to 97% ee) and moderate to good overall yield (up to 70%, for 3 steps), which were comparable to those of the conventional solution-phase methods. Furthermore, recovery and recycling of the polymer-supported chiral auxiliary were successfully achieved without decreasing the stereoselectivity of the product. Therefore, this is the first successful example that the solid-phase Evans' asymmetric enolate-alkylation was efficiently performed on the solid-support, and it is concluded that the connection to the solid-support via the 5-position of the oxazolidinone ring is an ideal strategy in the solid-phase Evans' chiral auxiliary.

Synthesis of prolyl endopeptidase inhibitors and evaluation of their structure-activity relationships: In vitro inhibition of prolyl endopeptidase from canine brain

By chemical modification of a known prolyl endopeptidase (PEP) inhibitor (N-[N-(4-phenylbutanoyl)-L-prolyl]pyrrolidine; SUAM-1221), several arylalkanoyl derivatives (V-1-27) were synthesized and tested for in vitro inhibitory activity towards PEP from canine brain. Among them, 4-(2- thienyl)butanoyl derivatives (V-24-27) showed more potent PEP-inhibitory activity than SUAM-1221. The structure-activity relationships of these compounds are discussed.

The total synthesis of the isodityrosine-derived cyclic tripeptides OF4949-III and K-13. Determination of the absolute configuration of K-13

The asymmetric syntheses of the two cyclic tripeptides OF4949-III and K-13 have been completed. The absolute stereochemical assignment of the former compound has been confirmed, while the absolute configuration of the latter has been established for the f