New strategies for protecting group chemistry: synthesis, reactivity, and indirect oxidative cleavage of para-siletanylbenzyl ethers.

Reported herein is a new entry in the growing arsenal of arylmethyl ether protecting groups. The para-siletanylbenzyl (PSB) ether is electronically similar to the benzyl ether. Cleavage of the PSB ether is accomplished under mild conditions--involving alkaline hydrogen peroxide--that are unique among cleavage protocols for arylmethyl ethers.

p-Siletanylbenzylidene acetal: oxidizable protecting group for diols.

[reactions: see text] Hydrogen peroxide oxidation of benzylidene acetals (and derivative benzyl ethers) that incorporate a siletane ring at the para position creates a deprotection pathway without affecting other important chemical properties of the benzylidene acetal, such as regioselective reductive ring opening.