81505-64-8

Basic information

• Product Name: N-[tert-Butyloxycarbonyl]-6-hydroxy-DL-norleucine
• Synonyms: N-[tert-Butyloxycarbonyl]-6-hydroxy-DL-norleucine;N-Boc-6-Hydroxy-DL-norleucine
• CAS NO: 81505-64-8
• Molecular Formula: C₁₁H₂₁NO₅
• Molecular Weight: 247.28814
• Product Categories: Chelating Agents & Ligands, Intermediates
• Mol File: 81505-64-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-[tert-Butyloxycarbonyl]-6-hydroxy-DL-norleucine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[tert-Butyloxycarbonyl]-6-hydroxy-DL-norleucine(81505-64-8)
• EPA Substance Registry System: N-[tert-Butyloxycarbonyl]-6-hydroxy-DL-norleucine(81505-64-8)

Safety Data

• Hazardous Substances Data: 81505-64-8(Hazardous Substances Data)

Usage

Uses

N-[tert-Butyloxycarbonyl]-6-hydroxy-DL-norleucine act as a reactant used in the preparation of Mycobactin and Aerobactin as iron chelator agents.

Upstream product

• 5462-80-6 rac-6-hydroxynorleucine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 305-77-1 L-ε-hydroxynorleucine 

Downstream Products

• 77611-38-2 (1-Benzyloxycarbamoyl-5-hydroxy-pentyl)-carbamic acid tert-butyl ester 
• 84063-93-4 (1-Benzyloxycarbamoyl-5-hydroxy-pentyl)-carbamic acid tert-butyl ester 
• 81505-49-9 (S)-(-)-Methyl 2-[(tert-butoxycarbonyl)amino]-6-hydroxypentanoate 
• 81505-49-9 (D,L)-N-Boc-ε-hydroxynorleucine methyl ester 
• 81505-51-3 (D,L)-N²-Boc-N⁶-acetyl-N⁶-(benzyloxy)lysine methyl ester 
• 81505-60-4 6-(Acetyl-benzyloxy-amino)-2-amino-hexanoic acid methyl ester 
• 81505-62-6 N²,N²-(anhydromethylene-1,5-citryl)bis6-acetyl-N⁶-(benzyloxy)-(L)-lysine methyl ester 
• 81505-63-7 N²,N²-(1,5-citryl)bis6-acetyl-N⁶-(benzyloxy)-(L)-lysine> 

Relevant articles and documents

Microbial Iron Chelators: Total Synthesis of Aerobactin and Its Constiruent Amino Acid, N6-Acetyl-N6-hydroxylysine

The synthesis of the natural ferric ionophore (-)-aerobactin (1) and of its constituent amino acid N6-acetyl-N6-hydroxylysine (2) is described.The benzyl hydroxamates * and ( were subjected to triphenylphosphine-diethyl azodicarboxylate-mediated alkylations with the ε-hydroxynorleucine derivative 7a.While * gave a complex mixture with predominant carbonyl O-alkylation, 9 was cleanly N-alkylated to yield 14.Compounds 10a,b were prepared by direct alkylation of 8 with bromides 15a,b which gave predominant N-alkylation.Hydrogenation of (D,L)-10a yielded (D,L)-N-6- acetyl-N6-hydroxylysine (2).Optically active 10b, prepared from (L)-ε-hydroxynorleucine, was α-N deprotected and coupled with anhydromethylenecitryl chloride (18) to yield 19, which was deprotected in two steps to yield (-)-aerobactin (1).