205808-16-8

Upstream product

• 259857-49-3 tert-butyl (3R)-3-methyl-2-oxopyrrolidine-1-carboxylate 
• 911634-58-7 (±)-methyl 4-(tert-butoxycarbonyl)amino-2-methylbutanoate 
• 259857-35-7 (S)-4-isopropyl-3-[(R)-2-methyl-4-nitrobutanoyl]-5,5-diphenyloxazolidin-2-one 
• 27948-40-9 (+)-3-methyl-2-pyrrolidinone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 136546-78-6 methyl (R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentanoate 
• 139462-29-6 (R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentanoic acid 
• 136546-79-7 <4S,3(2R)>-4-benzyl-3-<4-(tert-butoxycarbonyl)-2-methylbutanoyl>-2-oxazolidinone 
• 139462-30-9 <4S,3(2R)>-4-benzyl-3-<4-((tert-butoxycarbonyl)amino)-2-methylbutanoyl>-2-oxazolidinone 
• 55709-17-6 (S)-(-)-3-methyl-2-pyrrolidinone 

Relevant academic research and scientific papers

Effect of the Substituent and Amino Group Position on the Lipase-Catalyzed Resolution of γ-Amino Esters: A Molecular Docking Study Shedding Light on Candida antarctica lipase B Enantioselectivity

The kinetic resolution of N-tert-butoxycarbonyl γ-amino methyl esters bearing different stereocenters at alpha (γ2), beta (γ3), or gamma (γ4) positions was carried out by enantioselective hydrolysis with Candida antarctica lipase B (CaLB) in 2-methyl-2-butanol solvent. The results show that the process is significantly less enantioselective for the γ2-amino methyl ester (E=2.5), the γ3-amino methyl ester (E=7.6), and the γ4-amino methyl ester (E=8.3) when compared with the kinetic resolution of analogous N-protected β3-amino esters (E>80). Based on these results, molecular docking studies were carried out, through which particular regions in the CaLB catalytic cavity were analyzed. The steric exclusion region composed of Ile189 and Val190 residues, together with the amino bonding region that induces a hydrogen bond with the Asp134 residue, appear to be responsible for the high selectivity in the resolution of carboxylic acid derivatives with beta stereocenters. This interaction is well preserved for β-amino esters as substrates. By contrast, γ-amino esters exhibit greater conformational diversity, so the effectiveness of the interaction is reduced, which apparently is responsible for the loss of enantioselectivity in the resolution process.

CONJUGATES AND METHODS OF USING THE SAME

Disclosed are conjugates including a recognition element covalently bonded to or linked through a linker to a payload. The payload is a pharmaceutical agent (e.g., an antineoplastic agent, anti-infective agent, or anti-inflammatory agent) or a diagnostic agent. Also disclosed are methods of using the conjugates.

Enantioselective preparation of γ-amino acids and γ-lactams from nitro olefins and carboxylic acids, with the valine-derived 4-isopropyl-5,5- diphenyl-1,3-oxazolidin-2-one as an auxiliary

Titanium enolates of acyl-oxazolidinones 1, derived from acetic, propanoic, 3-methylbutanoic, and 4-methylpentanoic acids and 4-isopropyl-5,5- diphenyl-1,3-oxazolidin-2-one, are added to aliphatic and aromatic nitro olefins in the presence of TiCl4/

Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam

3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by α-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce γ-aminobutyric acid (GABA) analogue 13.

Asymmetric Synthesis of Calyculin A. 2. The C26-C37 γ-Amino Acid Fragments

New chiral imide enolate alkylation, aldol, and Michael addition bond constructions have been employed in the asymmetric synthesis of the C26-C37 portion of calyculin A.