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

Autor: Michiko Iwamura, Yuuki Hirayama, Toshiaki Furuta
Rok vydání: 2001
Předmět:
Zdroj: Organic letters. 3(12)
ISSN: 1523-7060
Popis: [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.
Databáze: OpenAIRE
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