3479-47-8

Usage

Uses

It is widely used as a pharmaceutical intermediate and in food industry.

InChI:InChI=1/C19H19NO6/c21-17(25-12-14-7-3-1-4-8-14)11-16(18(22)23)20-19(24)26-13-15-9-5-2-6-10-15/h1-10,16H,11-13H2,(H,20,24)(H,22,23)/t16-/m0/s1

Upstream product

• 5241-60-1 di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate 
• 2177-63-1 (S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid 
• 501-53-1 benzyl chloroformate 
• 100-55-0 3-hydroxymethylpyridin 
• 57933-83-2 Isopropenyl chloroformate 
• 1152-61-0 N-Cbz-L-Asp 
• 100-51-6 benzyl alcohol 
• 4515-23-5 N-benzyloxycarbonyl-L-aspartic acid anhydride 
• 104-15-4 toluene-4-sulfonic acid 

Downstream Products

• 6366-86-5 α-L-Asp-ε-L-Lys 
• 119278-21-6 N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-leucine benzyl ester 
• 2177-63-1 (S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid 
• 2304-96-3 N-benzyloxycarbonyl-L-asparagine 
• 23124-24-5 N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-tyrosine benzyl ester 
• 40470-02-8 N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-glycine benzyl ester 
• 5966-82-5 N²-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-N⁶-benzyloxycarbonyl-L-lysine benzyl ester 
• 13590-42-6 N-carboxy-L-aspartic anhydride benzyl ester 
• 35909-97-8 (S)-2-Benzyloxycarbonylamino-succinic acid 4-benzyl ester 1-methyl ester 
• 2419-54-7 N-(benzyloxycarbonyl)-β-benzyl-L-aspartic acid p-nitrophenyl ester 
• 51871-02-4 Z-Asp(OBzl)-Ser-OMe 
• 50833-34-6 (S)-2-((S)-3-Benzyloxycarbonyl-2-benzyloxycarbonylamino-propionylamino)-hexanoic acid methyl ester 
• 19653-70-4 (S)-6-Benzyloxycarbonylamino-2-((S)-3-benzyloxycarbonyl-2-benzyloxycarbonylamino-propionylamino)-hexanoic acid methyl ester 
• 61016-30-6 2-((S)-3-Benzyloxycarbonyl-2-benzyloxycarbonylamino-propionylamino)-malonic acid diethyl ester 

Relevant academic research and scientific papers

Asymmetric michael addition of malonates to enones catalyzed by a primary Β-amino acid and its lithium salt

Highly enantioselective Michael addition of malonates to enones was achieved using a mixed catalyst consisting of a primary Β-amino acid, O-TBDPS (S)-Β-homoserine, and its lithium salt. Various cyclic and acyclic enones were converted into 1,5-ketoesters in high yields (up to 92%) with high enantioselectivity (up to 97% ee) under mild reaction conditions. Details of synthesis of the catalyst, optimization of the reaction conditions for the Michael addition reaction, and a plausible reaction mechanism are described.

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 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.

Cleavage of Esters under Nearly Neutral Conditions at High Pressure. Chemo- and Regioselective Hydrolysis in Organic Solvents

Hydrolysis of esters proceeded at room temperature under high pressure in the presence of iPr2NEt or N-methylmorpholine using CH3CN-H2O (60:1) as the solvent.This very mild procedure enables the smooth hydrolysis of biologically important compounds such as amino esters, aliphatic unsaturated fatty esters, and β-hydroxy esters; no racemization, no isomerization, and no side reactions take place.

MONO-ESTERIFICATION OF N-PROTECTED DI-ACIDS ASPARTIC AND GLUTAMIC BY CHLOROFORMATE ACTIVATION

Mono-esters of N-protected di-acids aspartic and glutamic are prepared by a one-pot activation with alkyl chloroformates or isopropenyl chloroformate and an additionnal alcohol.This process involves the intermediate internal anhydride formation.

SYNTHETIC ENZYMES-4. HIGHLY ENANTIOSELECTIVE EPOXIDATION BY MEANS OF POLYAMINOACIDS IN A TRIPHASE SYSTEM: INFLUENCE OF STRUCTURAL VARIATIONS WITHIN THE CATALYSTS.

The asymmetric epoxidation of chalcone and other electron-poor olefins in a triphase system (water-organic solvent-polyaminoacid) affords optically active oxiranes.The influence of the molecular structure of catalysts and of their secondary conformation on the enantioselectivity of the reaction has also been examined.