128576-64-7

Upstream product

• 128576-63-6 (2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-39-0 benzyl bromide 
• 127605-48-5 (2S,3S)-2-Amino-3-benzyl-succinic acid 1-tert-butyl ester 4-methyl ester 
• 128576-60-3 1-tert-butyl 4-methyl (2S)-2-(benzylamino)butanedioate 
• 128576-65-8 (2S)-4-benzyl 1-tert-butyl N-benzylaspartate 
• 128576-61-4 1-(tert-butyl) 4-methyl N-benzyl-N-(9-phenyl-9H-fluoren-9-yl)-L-aspartate 
• 128599-28-0 (2S)-4-benzyl 1-tert-butyl N-benzyl-N-(9-phenylfluoren-9-yl)aspartate 
• 128576-67-0 (2S,3S)-1-tert-butyl N-benzyl-N-(9-phenylfluoren-9-yl)-3-benzylaspartate 
• 620-05-3 iodomethylbenzene 
• 128576-87-4 (2S,3S)-4-benzyl 1-tert-butyl N-benzyl-N-(9-phenylfluoren-9-yl)-3-benzylaspartate 
• 231302-86-6 (4S,5S)-3,4-Bis(tert-butoxylcarbonyl)-5-benzylidne-2,3,4,5-tetrahydro-6H-1,3-oxazin-6-one 
• 231302-87-7 (4S,5S)-3,4-Bis(tert-butoxycarbonyl)-5-benzyl-2,3,4,5-tetrahydro-6H-1,3-oxazin-6-one 
• 128576-62-5 (2S,3S)-1-tert-butyl 4-methyl N-benzyl-N-(9-phenylfluoren-9-yl)-3-benzylaspartate 

Downstream Products

• 128576-69-2 (4S,5S)-4-benzyl-1,5-bis(tert-butoxycarbonyl)-imidazolidin-2-one 

Relevant academic research and scientific papers

Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones

Oxazinones have been synthesised and used as chiral templates in the synthesis of β-substituted aspartic acids. Use of a Bredereck's reagent/Grignard/hydrogenation strategy gave cis-oxazinones with complete stereoselectivity, whereas an alkylation strategy, although trans-selective, gave mixtures of isomers. The oxazinones could be converted to β-substituted aspartic acids and to regioselectively protected β-substituted aspartic acids without loss of stereochemistry at either centre.

Tetrahydro-1,3-oxazin-6-ones as templates for the stereoselective synthesis of β-substituted L-aspartic acids

Protected (4S)-4-carboxytetrahydro-1,3-oxazin-6-ones have been synthesised either by Baeyer-Villiger reaction on a 4-ketoproline derivative or, more directly, from an aspartate derivative. Two strategies have been used to develop these compounds as chiral templates in the synthesis of β-substituted aspartic acids. In the first, formation of an enaminone using Bredereck's reagent, followed by reaction with a Grignard reagent gave a series of alkylidene derivatives which could be reduced from the less hindered side by heterogeneous catalytic hydrogenation to give cis-oxazinones in a completety stereoselective manner. Alternatively, an alkylation strategy, although trans-selective, gave mixtures of isomers. The oxazinones were converted to β-substituted aspartic acids and to regioselectively protected β-substituted aspartic acids without loss of stereochemistry ar either centre.

Stereoselective Synthesis of 2,3-Diamino Acids. 2,3-Diamino-4-phenylbutanoic Acid

The synthesis of (2S,3S)- and (2S,3R)-2,3-diamino-4-phenylbutanoic acid (1c and 3) from L-aspartic acid is described.The N-(phenylfluorenyl)-protected aspartic acid diesters 4 and 10 (α-tert-butyl, β-methyl), 18 (β-benzyl, α-tert-butyl), and 28 (β-benzyl,