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Anthraquinon-2-ylmethoxycarbonyl (Aqmoc):  A New Photochemically Removable Protecting Group for Alcohols

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journal contribution
posted on 17.05.2001, 00:00 by Toshiaki Furuta, Yuuki Hirayama, Michiko Iwamura
Synthesis and photochemistry of a new photochemically removable protecting group for alcohols is described. Four carbonates of galactose derivatives (14) 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 ∼106 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.