64143-96-0

Basic information

• Product Name: N-methyl-N-tosyl-L-leucine
• Synonyms: N-methyl-N-tosyl-L-leucine
• CAS NO: 64143-96-0
• Molecular Weight: 299.391
• Mol File: 64143-96-0.mol

Chemical Properties

• CAS DataBase Reference: N-methyl-N-tosyl-L-leucine(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-N-tosyl-L-leucine(64143-96-0)
• EPA Substance Registry System: N-methyl-N-tosyl-L-leucine(64143-96-0)

Safety Data

• Hazardous Substances Data: 64143-96-0(Hazardous Substances Data)

Upstream product

• 1220-80-0 (S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid 
• 50-00-0 formaldehyd 
• 98-59-9 p-toluenesulfonyl chloride 
• 61-90-5 L-leucine 
• 64143-84-6 (2S)-(N-para-toluenesulphonylamino)-4-methylpentanoic acid tert-butyl ester 
• 78797-30-5 (S)-4-Isobutyl-3-(toluene-4-sulfonyl)-oxazolidin-5-one 
• 64143-85-7 (S)-4-Methyl-2-[methyl-(toluene-4-sulfonyl)-amino]-pentanoic acid tert-butyl ester 

Downstream Products

• 3060-46-6 N-methyl-L-leucine 
• 106-45-6 para-thiocresol 
• 104-15-4 toluene-4-sulfonic acid 

Relevant articles and documents

Access to Optically Pure Benzosultams by Superelectrophilic Activation

Through superacid activation, N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel-Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereocenters in high yields with fully controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally restricted chiral dicationic intermediates.

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.

AN ALTERNATIVE ROUTE TO Nα-METHYLAMINO ACID DERIVATIVES: SYNTHESIS AND CONFORMATION OF SOME Nα-acetyl-Nα-METHYLAMINO ACID METHYLAMIDES

The methylation of tert-butyl- or isopropyl esters of Nα-4-toluenesulfonyl-amino acids by dimethylsulfate in aqueous alkaline solution in the presence of a detergent gives the corresponding Nα-methylderivatives.Using this synthetic route the Nα-acetylderivatives of MeAla, MeLeu, MeOrn and MePhe methylamides have been prepared and the solution conformation of these dipeptide units has been investigated. 1H and 13C NMR spectra show that, while in dimethylsulfoxide the tertiary amide group is mostly in cis-conformation, in protic solvents the equilibrium is shifted towards trans-conformation.Circular dichroism spectra reveal some specific features (e.g. high band intensities in protic solvents) which cannot be explained solely on the basis of the increased rigidity caused by the Nα-methyl group.We tried to explain these effects supposing that the tertiary amide group is deviated from the planar arrangement (due to the interaction between the methyl groups, a substituent on Cα and solvent molecule attached to the oxygen atom) and contributes to the observed circular dichroism as the inherently chiral chromophore.