Selective cleavage of methoxy protecting groups in carbohydrates

被引:27
作者
Boto, A [1 ]
Hernández, D [1 ]
Hernández, R [1 ]
Suárez, E [1 ]
机构
[1] CSIC, Inst Prod Nat & Agrobiol, San Cristobal la Laguna 38206, Tenerife, Spain
关键词
D O I
10.1021/jo052313o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The selective cleavage of methoxy protecting groups next to hydroxy groups is achieved using a radical hydrogen abstraction reaction as the key step. Under the reaction conditions, the hydroxy group generates an alkoxyl radical that reacts with the sterically accessible adjacent methoxy group, which is transformed into an acetal. In the second step, the acetals are hydrolyzed to give alcohols or diols. A one-pot hydrogen abstraction-hydrolysis procedure was also developed. Good yields were usually achieved, and the mild conditions of this methodology were compatible with different functional groups and sensitive substrates such as carbohydrates.
引用
收藏
页码:1938 / 1948
页数:11
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