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Usage

Uses

Used in Pharmaceutical Industry:
N-tosyl-L-aspartic acid is used as an intermediate in the synthesis of various pharmaceutical compounds. Its role in this application is attributed to its ability to protect the L-Aspartic Acid during the chemical reactions, ensuring the successful formation of the desired products.
Used in Chemical Synthesis:
In the field of chemical synthesis, N-tosyl-L-aspartic acid is utilized as a protecting group for L-Aspartic Acid. This protection is crucial for preventing unwanted side reactions and ensuring the selective functionalization of the amino acid, leading to the production of specific target molecules.
Used in Research and Development:
N-tosyl-L-aspartic acid is also employed in research and development for the study of amino acid chemistry and its applications in various biological processes. Its protective nature allows researchers to explore the potential of L-Aspartic Acid in different contexts, such as enzyme catalysis and protein structure.
Used in Food Industry:
Although not explicitly mentioned in the provided materials, N-tosyl-L-aspartic acid may also find applications in the food industry, particularly in the development of flavor enhancers and additives. Its role in this industry would be to protect L-Aspartic Acid during the manufacturing process, ensuring the preservation of its taste-enhancing properties.

InChI:InChI=1/C11H13NO6S/c1-7-2-4-8(5-3-7)19(17,18)12-9(11(15)16)6-10(13)14/h2-5,9,12H,6H2,1H3,(H,13,14)(H,15,16)/t9-/m0/s1

Upstream product

• 56-84-8 L-Aspartic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 5454-85-3 N-(toluene-sulfonyl-⁽⁴⁾)-L-aspartic acid dibutyl ester 
• 21440-07-3 (-)-(3S)-3,4-dihydro-3-(tosylamino)furan-2,5-dione 
• 95331-51-4 N-[(4-methylphenyl)sulfonyl]-L-aspartic acid 1,4-dimethyl ester 
• 147136-78-5 N-(3-hydroxy-1-hydroxymethyl-propyl)-4-methylbenzenesulfonamide 
• 104830-35-5 N-[(4-methylphenyl)sulfonyl]-L-aspartic acid 1,4-diethyl ester 
• 10396-97-1 4-methyl-N-((S)-2-oxotetrahydrofuran-3-yl)benzenesulfonamide 
• 207791-14-8 (S)-N-nosylhomoserine γ-lactone 
• 88613-49-4 (S)-3-[(4-methylphenyl)sulfonyl]-5-oxo-4-oxazolidineacetic acid 
• 1316250-70-0 (S)-3-[(2-nitrophenyl)sulfonyl]-5-oxo-4-oxazolidineacetic acid 
• 147228-23-7 (3R)-ethyl 3-(tosylamino)pentanoate 
• 147228-29-3 (3R)-3-(tosylamino)pentanoic acid 
• 147228-27-1 (3R)-ethyl 5-phenyl-3-(tosylamino)pentanoate 
• 147228-33-9 (3R)-5-phenyl-3-(tosylamino)pentanoic acid 
• 147228-25-9 (3R)-ethyl 5,5-dimethyl-3-(tosylamino)hexanoate 

Relevant academic research and scientific papers

A practical method for selective cleavage of a tert-butoxycarbamoyl N-protective group from N,N-diprotected α-amino acid derivatives using montmorillonite K-10

A new, practical, and mild procedure for the selective cleavage of a tert-butoxycarbonyl group (Boc) in N-Boc-N-acyl-diprotected amines is described. When applied to α-amino acids, complete integrity of the stereochemistry was observed. The use of N,N-di-Boc-α-amino-δ- and γ-hydroxy esters provided both δ- and γ-lactones in very good yields. The method is based on the use of Montmorillonite K-10 either in CH 2Cl2 at room temperature or in toluene at 65°C and is compatible with the presence of a large range of functional and other protecting groups in the substrates. In most cases virtually pure samples are obtained after filtration and removal of solvents. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Total syntheses of the spermine alkaloids (-)-(R,R)-hopromine and (±)-homaline

The diastereoselective synthesis of the spermine alkaloid (R,R)-hopromine (2) is described. The as yet unknown absolute configuration of naturally occurring (-)-hopromine (2) is (R,R) and was established by comparison of the reported specific rotation of the natural product with that of the synthetic one. Preparation of the characteristic bis-8-membered lactam scaffold was carried out by convergent build-up of basic chiral azalactam units 21a and 21b and subsequent iterative linking (Schemes 5 and 6). Key steps in the analogous syntheses of 4-alkyl-hexahydro-1,5-diazocin-2(1H)-ones 21a and 21b were the introduction of the unbranched alkyl side chains into their common precursor 14 via cuprate reaction and the Sb(OEt)3-assisted cyclization of the open-chain intermediates 20a and 20b, respectively (Schemes 3 and 4). The chiral iodoester 14 was prepared from commercially available (+)-L-aspartic acid (12). Based on the synthetic strategy developed for (R,R)-hopromine (2), a rapid access to the parent alkaloid homaline (1) in its (±)-form is given.

HIV protease inhibitors based on amino acid derivatives

A compound selected from the group consisting of a compound of formula I 1a compound of formula II 2and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R1, R2, Cx, n, R3, R4, R5, Y are as defined in the specification.

104. The enantioselective synthesis of β-amino acids, their α-hydroxy derivatives, and the N-terminal components of bestatin and microginin

L-Aspartic acid by tosylation, anhydride formation, and reduction with NaBH4 was converted into (3S)-3-(tosylamino)butan-4-olide (8; Scheme 1). Treatment of 8 with ethanolic trimethylsilyl iodide gave the N-protected deoxy-iodo-β-homoserine ethyl ester 9. The latter, on successive nucleophilic displacement with lithium dialkylcuprates (→ 10a-e), alkaline hydrolysis (→ 11a-e), and reductive removal of the tosyl group, produced the corresponding 4-substituted (3R)-3-aminobutanoic acids 12a-e (ee >99%). Electrophilic hydroxylation of 8 (→ 19; Scheme 3), subsequent iodo-esterification (→ 21; Scheme 4), and nucleophilic alkylation and phenylation afforded, after saponification and deprotection, a series of 4-substituted (2S,3A)-3-amino-2-hydroxybutanoic acids 24 including the N-terminal acids 24e (= 3) and 24f (= 4) of bestatin and microginin (de >95%), respectively.

A practical synthesis of (2S,3R)-3-amino-2-methylpentanoic acid from L-aspartic acid

L-Aspartic acid by successive N-tosylation, anhydride formation, and reduction was converted into (3S)-3-(tosylamino)butano-4-lactone (4). Electrophilic methylation of 4, subsequent iodo-esterification and nucleophilic methylation, followed by saponification and deprotection, gave (2S,3R)-3-amino-2-methylpentanoic acid (2) with an ee of > 99%in seven steps and in an overall yield of 34%.

An enantiospecific synthesis of β-amino acids

L-Aspartic acid by regioselective modification of the α-carboxylic acid group, namely N-tosylation, anhydride formation, reduction, iodo-esterification, alkylation, and deprotection afforded a series of γ-alkyl β-aminobutyric acids of the R configuration (ee > 99%).

Process for the manufacture of (S)-3-amino-1-substituted-pyrrolidines

A novel process for preparing a stereospecific (S)-3-amino-1-substituted pyrrolidine used as a key intermediate in preparing quinolone and naphthyridone antibacterial agents where the 7-position is occupied with a sterospecific 3-amino-pyrrolidine side chain is described starting from inexpensive L-aspartic acid. L-aspartic acid is converted to the desired (S)-3-aminopyrrolidine via a novel, high yield transformation of a substituted aziridine.