Anthraquinon-2-ylmethoxycarbonyl (Aqmoc): A new photochemically removable protecting group for alcohols

[GRAPHICS] Synthesis and photochemistry of a new photochemically removable protecting group for alcohols is described. Four carbonates of galactose derivatives (1-4) were synthesized from the corresponding arylmethanols via 4-nitrophenyl carbonate intermediates. Among them, photolysis of anthraquinon-2-ylmethoxycarbonyl (Aqmoc) galactose (1) proceeded with overall photolysis efficiency of 150 (quantum yield 0.10, and molar absorptivity 1500 M-1 cm(-1)) and rate constant of similar to 10(6) s(-1). To demonstrate its application to a biologically related molecule, 5 ' -Aqmoc-adenosine (5) was synthesized and photolyzed to yield adenosine in 91% yield.