524675-10-3

Upstream product

• 88999-92-2 2-(4-bromophenyl)ethane-1-thiol 
• 4163-60-4 β-D-galactose peracetate 
• 4654-39-1 4-bromophenethanol 
• 114369-15-2 2-(4-bromophenyl)ethyl methanesulfonate 
• 253443-13-9 S-[2-(4-bromophenyl)ethyl]thioacetate 

Downstream Products

• 524675-12-5 2-(4-iodophenyl)ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of radioiodine-labeled 2-phenylethyl 1-thio-β-D-galactopyranoside for imaging of LacZ gene expression

A potent inhibitor of β-galactosidase (EC 3.2.1.23), 2-phenylethyl 1-thio-β-D-galactopyranoside (PETG), was radioiodinated for noninvasive imaging of LacZ gene expression. In order to introduce radioiodine to the phenyl ring of PETG, 2-(4-bromophenyl)ethanethiol was prepared and attached to the C-1 position of β-D-galactose pentaacetate under conditions that resulted in the exclusive formation of the β anomer. The bromo group of PETG was converted to the tributylstannyl group where radioiododemetallation was carried out. Radioiodine-labeled PETG tetraacetate was purified by HPLC, which can be used as a prodrug for biological evaluation or hydrolyzed to 2-(4-[123I/125I]iodophenyl)ethyl 1-thio-β-D-galactopyranoside ([123I/125I]7) under basic conditions. The resulting radioiodine-labeled PETG was obtained in overall 62% radiochemical yield (decay-corrected) and with specific activity of 46-74 GBq/μmol.