1-[2-(Trimethylsilyl)ethoxy]ethyl (SEE): A novel hybrid hydroxy-protecting group between 1-(ethoxy)ethyl (EE) and 2-(trimethylsilyl)ethoxymethyl (SEM)

Article abstract of DOI:10.1016/0040-4039(96)00663-6

The highly versatile 1-[(2-trimethylsilyl)ethoxy]ethyl (SEE) group, readily obtainable from an alcohol and 2-(trimethylsilyl)ethyl vinyl ether in the presence of a catalytic amount of PPTS, has been developed for the protection of hydroxyl groups. Its deprotection can be achieved under virtually neutral conditions with the use of a fluoride ion source, thus allowing for effective protection of hydroxyl groups of compounds that contain acid- and/or base-sensitive functional groups.