Selective cleavage of methoxy protecting groups in carbohydrates.
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.
Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sanchez 3, 38206-La Laguna, Tenerife, Spain. alicia@ipna.csic.es
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D000080:Acetals / Q000737:chemistry*; D000085:Acetates / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D006868:Hydrolysis
D000080:Acetals; D000085:Acetates; D002241:Carbohydrates; D006859:Hydrogen; D005947:Glucose; C046923:methyl acetate; D005690:Galactose