55024-57-2

Upstream product

• 55024-33-4 N^α-Acetyl-N^ε-tosyl-N^ε-benzyloxy-L-lysin-anilid 
• 161264-10-4 (2R)-N-<(2S)-6--2-<amino>hexanoyl>bornane-10,2-sultam 
• 161264-05-7 (2R)-N-<<>(2S)-2-<amino>-6-iodohexan-1-oyl>bornane-10,2-sultam 
• 1576-39-2 O-benzyl-N-tosylhydroxylamine 
• 55061-85-3 4-(N-Tosyl-N-benzyloxy)aminobutylbromid 
• 55024-55-0 N^α-Acetyl-N^ε-tosyl-N^ε-benzyloxy-DL-lysin 
• 55024-34-5 N^ε-Tosyl-N^ε-benzyloxy-DL-lysin 

Downstream Products

• 55024-36-7 (S)-N^ε-(benzyloxy)lysine 

Relevant academic research and scientific papers

Asymmetric alkylations of a sultam-derived glycine equivalent: Practical preparation of enantiomerically pure α-amino acids

Alkylation of the chiral glycine derivative 2 with 'activated' organohalides under ultrasound-assisted phase-transfer catalysis or with activated and nonactivatcd organohalides in anhydrous medium provides (mostly crystalline) alkylation products 3. Acidic hydrolysis of the pure products 3 gives (aminoacyl)sultams 4 which by mild saponification furnish pure α-amino acids 5 in good overall yields from 2, along with recovered auxiliary 1 (Scheme 1). Pure ω-protected α,ω-diamino acids and α-amino-ω-(hydroxyamino)acids 12-16 are readily accessible from (ω-haloacyl)sultams 3 via reaction with N-nucleophiles followed by acidic and basic hydrolyses (Scheme 2). A reliable determination of the enantiomeric purity of α-amino acids using HPLC analysis of their N-(3,5-dinitrobenzoyl)prolyl derivatives 17 is presented.