856433-05-1

Upstream product

• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 20566-48-7 2-[(4-methoxyphenyl)methyl]acrylic acid ethyl ester 
• 856433-01-7 2-[(4-methoxyphenyl)methyl]prop-2-en-1-ol 
• 182316-18-3 (5S)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide 

Downstream Products

• 856433-10-8 (2S,4S)-4-(tert-butoxycarbonyl)amino-2-[(4-methoxyphenyl)methyl]-5-oxooxolane-2-carboxylic acid 
• 856433-09-5 (2S,4S)-4-(tert-butoxycarbonyl)amino-2-[(4-methoxyphenyl)methyl]-2-(hydroxymethyl)oxolan-5-one 

Relevant academic research and scientific papers

Stereoselective syntheses of 4-hydroxy 4-substituted glutamic acids

The 4-hydroxy 4-substituted glutamic acid moiety is a common substructure of biologically important natural products such as monatin [(2S,4S)-2], lycoperdic acid (3), and dysiherbaine (4). To develop methodology for syntheses of these natural products, cycloadditions of nitrone 5 with 2-substituted 2-propen-1-ols 6 and 2-substituted acrylates 8 were investigated. Reactions of nitrone 5 with alcohols 6 in the presence of MgBr2OEt2 gave cycloadducts 7 in a highly stereoselective manner, whereas noncatalyzed reactions of 5 with acrylates 8 afforded adducts 9. Using the former reaction, syntheses of monatin [(2S,4S)-2], monatin derivative 18, and lycoperdic acid (3) were accomplished. The C4-epimer of monatin [(2S,4R)-2)] was also synthesized by employing the latter cycloaddition.