151842-29-4

Basic information

• Product Name: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-(tributylstannyl)-, methyl ester
• CAS NO: 151842-29-4
• Molecular Formula: C27H47NO4Sn
• Molecular Weight: 568.384
• Mol File: 151842-29-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-(tributylstannyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-(tributylstannyl)-, methyl ester(151842-29-4)
• EPA Substance Registry System: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-(tributylstannyl)-, methyl ester(151842-29-4)

Safety Data

• Hazardous Substances Data: 151842-29-4(Hazardous Substances Data)

Upstream product

• 813-19-4 bis(tri-n-butyltin) 
• 113850-76-3 N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester 
• 112766-18-4 methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate 

Downstream Products

• 134362-34-8 methyl 2-(S)-((tert-butoxycarbonyl)amino)-3-(4'-fluorophenyl)propanoate 
• 1325730-41-3 N-Boc-4-(trifluoromethoxy)-L-phenylalanine methyl ester 
• 193420-27-8 N-tert-butoxycarbonyl-4-(pyridin-3-yl)-L-phenylalanine methyl ester 
• 343981-03-3 4-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester 

Relevant articles and documents

A convenient and reproducible method for the synthesis of astatinated 4-[211At]astato-l-phenylalanine: Via electrophilic desilylation

The 211At-labeled compound, 4-[211At]astato-l-phenylalanine, is one of the most promising amino acid derivatives for use in targeted alpha therapy (TAT) for various cancers. Electrophilic demetallation of a stannyl precursor is the most widely used approach for labeling biomolecules with 211At. However, the low acid-resistance of the stannyl precursor necessitates the use of an N- and C-terminus-protected precursor, which results in a low overall radiochemical yield (RCY) due to the multiple synthetic steps involved. In this study, a deprotected organosilyl compound, 4-triethylsilyl-l-phenylalanine, was employed for the direct synthesis of astatinated phenylalanines. 211At was separately recovered from the irradiated 209Bi target using chloroform (CHCl3) and N-chlorosuccinimide-methanol (NCS-MeOH) solution. The RCYs of 4-[211At]astato-l-phenylalanine obtained from the triethylsilyl precursor with the use of 211At, isolated in CHCl3 and NCS-MeOH solution, were 75% and 64% respectively. In both cases, the retention time of the 4-[211At]astato-l-phenylalanine was found to be about 20 min, which showed reasonable correlation with the retention time of non-radioactive 4-halo-l-phenylalanines (4-chloro-, 4-bromo-, and 4-iodo-l-phenylalanine). The one-step reaction examined in this study involved mild reaction conditions (70 °C) and a short time (10 min) compared to the other currently reported procedures for astatination. Electrophilic desilylation was found to be very effective for the labeling of aromatic amino acids with 211At.

4-Pyrimidinyl-n-acyl-l phenylalanines

Compounds of Formula I are disclosed, having activity as inhibitors of binding between VCAM-1 and cells expressing VLA-4, and accordingly useful for treating diseases whose symptoms and or damage are related to the binding of VCAM-1 to cells expressing VLA-4.