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.

引用

页码：1809 / 1812

页数：4

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