172941-42-3

Basic information

• Product Name: methyl 3N-benzylaminododecanoate
• CAS NO: 172941-42-3
• Molecular Weight: 319.488
• Mol File: 172941-42-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 3N-benzylaminododecanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3N-benzylaminododecanoate(172941-42-3)
• EPA Substance Registry System: methyl 3N-benzylaminododecanoate(172941-42-3)

Safety Data

• Hazardous Substances Data: 172941-42-3(Hazardous Substances Data)

Upstream product

• 112-31-2 caprinaldehyde 
• 6208-91-9 methyl (E)-dodec-2-enolate 
• 100-46-9 benzylamine 

Downstream Products

• 248605-41-6 cyclo (Gly-L-Lys(Z)-L-Val-3(S)-aminododecanoyl-) 
• 172941-85-4 cyclo (Gly-L-Lys(Z)-L-Val-3(R)-aminododecanoyl-) 

Relevant articles and documents

Rhodopeptins, novel cyclic tetrapeptides with antifungal activities from Rhodococcus sp.. III. Synthetic study of rhodopeptins

Total syntheses of cyclo (-Gly-L-Lys-L-Val-(R)-3-aminododecanoyl-); LV9nA and its diastereomer cyclo (-Gly-L-Lys-L-Val-(S)-3-aminododecanoyl-); LV9nB, congeners of rhodopeptin B5 on β-amino acid moiety, were achieved. The β-amino acid moiety was prepared as a racemate by the thermal Michael addition of an amine to α,β-unsaturated ester. The racemic β-amino acids were converted to their L-Valylamide derivatives and the obtained diastereomers were separated. Coupling of both diastereomers, L-Val-β-amino acids with Gly-L-Lys gave linear tetrapeptides, and tetrapeptides were cyclized by diphenylphosphoryl azide (DPPA) method between C-terminus of β-amino acid and N-terminus of Gly to give cyclic tetrapeptides. The deprotected cyclic tetrapeptides, LV9nA and LV9nB, both exhibited almost the same antifungal activity as the naturally obtained rhodopeptins. Furthermore, comparison of the 1H NMR spectra of two congeners and rhodopeptin B5 suggested that the stereochemistry of β-amino acid moiety in natural rhodopeptin B5 has (R)-configuration.