1384458-03-0

Basic information

• Product Name: N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester
• Synonyms: N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester
• CAS NO: 1384458-03-0
• Molecular Weight: 585.635
• Mol File: 1384458-03-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester(1384458-03-0)
• EPA Substance Registry System: N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-2-(diethoxyphosphoryl)glycine methyl ester(1384458-03-0)

Safety Data

• Hazardous Substances Data: 1384458-03-0(Hazardous Substances Data)

Upstream product

• 122-52-1 triethyl phosphite 
• 1402348-91-7 N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-L-threonine methyl ester 
• 7801-71-0 N-benzyloxycarbonyl-L-leucyl-L-leucine 

Downstream Products

• 1384458-04-1 (Z)-N-(N-benzyloxycarbonyl-L-leucyl-L-leucyl)-α,β-dehydro-5-(phenyl)norvaline methyl ester 

Relevant articles and documents

Metal-Free, Site-Selective Peptide Modification by Conversion of “Customizable” Units into β-Substituted Dehydroamino Acids

Our site-selective modification of serine or threonine units in peptides allows the generation of β-substituted dehydroamino acids, which increase peptide resistance to hydrolysis and may improve their biological properties. Both the terminal and internal positions can be modified, and different customizable units can be activated separately. Remarkably, high Z selectivity is achieved, even at internal positions. The conversion involves a one-pot oxidative radical scission/phosphorylation process by using the low-toxicity (diacetoxyiodo)benzene/iodine system as the scission reagent. The resulting α-amino phosphonates undergo a Horner-Wadsworth-Emmons reaction to produce the dehydroamino acid derivatives (in a Z/E ratio of usually >98:2) under mild and metal-free conditions.