147228-33-9

Basic information

• Product Name: (3R)-5-phenyl-3-(tosylamino)pentanoic acid
• Synonyms: (3R)-5-phenyl-3-(tosylamino)pentanoic acid
• CAS NO: 147228-33-9
• Molecular Weight: 347.435
• Mol File: 147228-33-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3R)-5-phenyl-3-(tosylamino)pentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-5-phenyl-3-(tosylamino)pentanoic acid(147228-33-9)
• EPA Substance Registry System: (3R)-5-phenyl-3-(tosylamino)pentanoic acid(147228-33-9)

Safety Data

• Hazardous Substances Data: 147228-33-9(Hazardous Substances Data)

Upstream product

• 21440-07-3 (-)-(3S)-3,4-dihydro-3-(tosylamino)furan-2,5-dione 
• 98-59-9 p-toluenesulfonyl chloride 
• 4816-82-4 N-[(4-methylphenyl)-sulfonyl]-L-aspartic acid 
• 147228-22-6 ethyl (-)-(3S)-4-iodo-3-(tosylamino)butanoate 
• 147228-21-5 (S)-4-<(tolylsulfonyl)amino>-γ-butyrolactone 
• 147228-27-1 (3R)-ethyl 5-phenyl-3-(tosylamino)pentanoate 

Downstream Products

• 147228-37-3 (3R)-3-amino-5-phenylpentanoic acid 

Relevant articles and documents

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.