Anthraquinon-2-ylmethoxycarbonyl (Aqmoc): a new photochemically removable protecting group for alcohols.
[see structure]. 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) x cm(-1)) and rate constant of approximately 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.
Furuta
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T
PRESTO, JST, and Department of Biomolecular Science, Toho University, 2-2-1 Miyama, Funabashi, 274-8510 Japan. furuta@biomol.sci.toho-u.ac.jp
Hirayama
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Y
Iwamura
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M