130568-14-8

Basic information

• Product Name: 2-(t-butyloxycarbonylamino)-4-(dimethylphosphono)butanoylleucine benzyl ester
• Synonyms: 2-(t-butyloxycarbonylamino)-4-(dimethylphosphono)butanoylleucine benzyl ester
• CAS NO: 130568-14-8
• Molecular Weight: 514.556
• Mol File: 130568-14-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-(t-butyloxycarbonylamino)-4-(dimethylphosphono)butanoylleucine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(t-butyloxycarbonylamino)-4-(dimethylphosphono)butanoylleucine benzyl ester(130568-14-8)
• EPA Substance Registry System: 2-(t-butyloxycarbonylamino)-4-(dimethylphosphono)butanoylleucine benzyl ester(130568-14-8)

Safety Data

• Hazardous Substances Data: 130568-14-8(Hazardous Substances Data)

Upstream product

• 2462-35-3 L-leucine benzyl ester hydrochloride 
• 120286-26-2 (S)-2-(tert-Butyloxycarbonylamino)-4-dimethoxyphosphorylbutanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 130568-08-0 (2S)-2-amino-4-(dimethylphosphono)butanoic acid trifluoroacetate 
• 130568-05-7 t-butyl (2S,4RS)-2-(t-butoxycarbonylamino)-4-(dimethylphosphono)-4-(imidazolylthiocarbonyloxy)butanoate 
• 130568-04-6 t-butyl (2S,4RS)-2-(t-butoxycarbonylamino)-4-(dimethylphosphono)-4-hydroxybutanoate 
• 130568-06-8 t-butyl (2S)-2-(t-butyloxycarbonylamino)-4-(dimethylphosphono)butanoate 

Downstream Products

• 130568-16-0 (S)-2-[(S)-2-Amino-4-(dimethoxy-phosphoryl)-butyrylamino]-4-methyl-pentanoic acid benzyl ester; compound with trifluoro-acetic acid 

Relevant articles and documents

The Improved Synthesis of Boc-Abu(PO3Me2)-OH and its Use for the Facile Synthesis of Glu-Abu(P)-Leu

The improved synthesis of Boc-L-Abu(PO3Me2)-OH from Boc-Asp-OBut in 42percent overall yield is described.This derivative was prepared in seven steps and involved initial sodium borohydride reduction of the isobutoxycarbonyl mixed anhydride of Boc-Asp-OBut and subsequent 2,2,6,6-tetramethylpiperidine-1-oxyl-catalysed sodium hypochlorite oxidation of the alcohol.The resultant aldehyde was phosphonylated by reflux with dimethyl trimethylsilyl phosphite and the trimethylsilyl group was then cleaved in situ by aqueous hydrolysis.The 4-hydroxy 4-dimethylphosphono derivative was converted into the Abu(PO3Me2) residue by reaction with thiocarbonyldiimidazole followed by radical deoxygenation of the thiocarbonylimidazolide with tributyltin hydride.The Boc and t-butyl groups were cleaved from Boc-Abu(PO3Me2)-OBut with trifluoroacetic acid and the Boc group was reintroduced to H-Abu(PO3Me2)-OH by using di-t-butyl dicarbonate to give Boc-Abu(PO3Me2)-OH as a clear oil.The optical purity of the Abu(PO3Me2) residue was established to be greater than 99.5percent of the L-isomer by h.p.l.c. analysis of its L-Leu dipeptide.The protected derivative Boc-Abu(PO3Me2)-OH was used in the Boc mode of peptide synthesis for the preparation of Boc-Glu(OBzl)-Abu(PO3Me2)-Leu-OBzl in high yield, 40percent CF3CO2H/CH2Cl2 being used for cleavage of the Boc group from intermediate peptides.The tripeptide was deprotected to H-Glu-Abu(P)-Leu-OH by a two-step procedure which involved initial hydrogenolytic cleavage of the benzyl groups in 50percent CF3CO2H/CH3CO2H followed by cleavage of the methyl phosphate groups with either (A) 30percent bromotrimethylsilane in acetonitrile, or (B) 1 M bromotrimethylsilane/1 M thioanisole in trifluoroacetic acid; complete cleavage of the methyl groups was effected after 40 min and 12 h, respectively.In addition, the dipeptide Boc-Leu-Abu(PO3Me2)-OBut was prepared from Boc-Abu(PO3Me2)-OBut in high yield and was readilly deprotected by acidolytic cleavage of the t-butyl groups with trifluoroacetic acid followed by silylitic cleavage of the methyl phosphonate groups with 30percent bromotrimethylsilane in acetonitrile, H-Leu-Abu(P)-OH being obtained in high yield.