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

被引：59
作者：
Furuta, T
Hirayama, Y
Iwamura, M
机构：
[1] JST, PRESTO, Funabashi, Chiba 2748510, Japan
[2] Toho Univ, Dept Biomol Sci, Funabashi, Chiba 2748510, Japan
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 12期
关键词：
D O I：
10.1021/ol015787s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[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.
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收藏
页码：1809 / 1812
页数：4
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