42417-66-3

Basic information

• Product Name: N-Cbz-N-methyl-L-isoleucine
• Synonyms: BENZYLOXYCARBONYL-N-ALPHA-METHYL-L-ISOLEUCINE;BENZLOXYCARBONYL-N-METHYL-L-ISOLEUCINE;N-ALPHA-CBZ-N-ALPHA-METHYL-L-ISOLEUCINE;N-ALPHA-CARBOBENZOXY-N-ALPHA-METHYL-L-ISOLEUCINE;N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-L-ISOLEUCINE;Z-MEILE-OH;Z-L-MEILE-OH;Z-N-METHYL-L-ISOLEUCINE
• CAS NO: 42417-66-3
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Product Categories: Amino Acid Derivatives
• Mol File: 42417-66-3.mol
• Article Data: 4

Chemical Properties

• Appearance: White to off-white/Powder
• Storage Temp.: Store at RT.
• CAS DataBase Reference: N-Cbz-N-methyl-L-isoleucine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-N-methyl-L-isoleucine(42417-66-3)
• EPA Substance Registry System: N-Cbz-N-methyl-L-isoleucine(42417-66-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 42417-66-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Upstream product

• 73-32-5 L-isoleucine 
• 3160-59-6 N-Cbz-L-Isoleucine 
• 66866-65-7 phenylmethyl (4S)-4-[(1S)-1-methylpropyl]-5-oxo-1,3-oxazolidine-3-carboxylate 
• 3160-59-6 N-benzyloxycarbonyl-L-isoleucine 
• 74-88-4 methyl iodide 

Downstream Products

• 922705-71-3 phenylmethyl [(1S,2S)-1-(diazoacetyl)-2-methylbutyl]methylcarbamate 
• 95866-68-5 Z-N-Methyl-L-isoleucyl-D-α-hydroxy-isovaleriansaeure 
• 1140836-72-1 (2S,3S)-tert-butyl 2-((benzyloxycarbonyl)(methyl)amino)-3-methylpentanoate 
• 1140836-24-3 (S)-benzyl 1-((2S,3S)-2-((benzyloxycarbonyl)(methyl)amino)-3-methylpentanoyl)piperidine-2-carboxylate 
• 1438853-29-2 N-{(2R,3R)-3-methoxy-3-[(2S)-1-{(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoyl]pyrrolidin-2-yl]-2-methylpropanoyl]-L-phenylalanine 
• 1438852-80-2 pentafluorophenyl (3R,4S,5S)-4-[{N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl}(methyl)amino]-3-methoxy-5-methylheptanoate 

Relevant articles and documents

Determination of the complete absolute configuration of petriellin A

We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey's derivatives and Marfey's derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids. CSIRO 2006.

A simple and rapid protocol for N-methyl-α-amino acids

A two step strategy for optically pure N-Protected-N-methyl-α-amino acids starting from N-protected-α-amino acids via reductive cleavage of oxazolidinones using NaCNBH3/TMSCl is described.