The sisyl (tris(trimethylsilyl)silyl) group: A fluoride resistant, photolabile alcohol protecting group

The use of the tris(trimethylsilyl)silyl (sisyl) group as a photolabile protecting group for primary and secondary alcohols was demonstrated. Sisyl ethers of a number of alcohols (yields 70–97%) were stable to many synthetic protocols, but could be deprotected using photolysis to give the starting alcohols (yields 62–95%).