Anthraquinon-2-ylmethoxycarbonyl (Aqmoc): a new photochemically removable protecting group for alcohols
Autor: | Michiko Iwamura, Yuuki Hirayama, Toshiaki Furuta |
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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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