224797-56-2

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 224797-50-6 (2R,5R)-5-hydroxy-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octan-8-one 
• 134107-65-6 (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 
• 190850-55-6 (3R)-5-tert-butyldimethylsiloxy-3-phenyl-1H-pyrrolo[1,2-c]oxazole 

Downstream Products

• 174283-18-2 (S)-methyl 2-(hydroxymethyl)-5-oxopyrrolidine-2-carboxylate 
• 793682-88-9 (2S,4S)-4-hydroxy-2-hydroxymethyl-2-methoxycarbonyl-1-methylpyrrolidin-5-one 
• 793682-85-6 (5R,7R)-5-cyano-7-hydroxy-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octan-8-one 
• 793682-84-5 (5R,7S)-5-cyano-7-hydroxy-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octan-8-one 

Relevant academic research and scientific papers

Nitrone [2+3]-cycloadditions in stereocontrolled synthesis of a potent proteasome inhibitor: (-)-Omuralide

(Chemical Equation Presented) A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, β-eliminations, and highly selective hydrogenations as the main steps.

Diastereoselective syntheses of deoxydysibetaine, dysibetaine, and its 4-epimer

(±)-Deoxydysibetaine 2 and 4-epi-dysibetaine 3 were prepared in a few steps from methyl pyroglutamate through a regioselective Mannich reaction at C-2. Natural (2S,4S)-dysibetaine 1, a sponge metabolite isolated from Dysidea herbacea, and (2S)-2 were synt

Stereoselective synthesis of (2S)-2-hydroxymethylglutamic acid, a potent agonist of metabotropic glutamate receptor mGluR3

Straightforward stereocontrolled synthesis of (2S)-2-hydroxymethylglutamic acid was achieved from (S)-pyroglutaminol, through a bicyclic silyloxypyrrole derived from the versatile unsaturated lactam 3.

Tandem electrophilic and nucleophilic additions to bicyclic tert- butyldimethylsilyloxypyrrole derived from (S)-pyroglutaminol

The silyloxypyrrole derivative 3, treated with SnCl4 and aqueous NaHCO3, afforded the 5-hydroxylated pyrrolidinone 7. This compound was shown to be a key intermediate for the diastereoselective introduction of other hetero- and C-nucleophiles at the same position.