792944-01-5Relevant academic research and scientific papers
Selective cleavage of methoxy protecting groups in carbohydrates
Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo,Suarez, Ernesto
, p. 1938 - 1948 (2007/10/03)
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.
Efficient and selective removal of methoxy protecting groups in carbohydrates
Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo,Suarez, Ernesto
, p. 3785 - 3788 (2007/10/03)
(Chemical Equation Presented) The selective removal from carbohydrate substrates of methoxy protecting groups next to hydroxy groups is reported. On treatment with Phl(OAc)2-I2, the methoxy group is transformed into an easily removable acetal. The mild conditions of this methodology are compatible with many functional groups, and good to excellent yields are usually achieved.
