SEM-作为羟基的保护基，其主要特点为最后脱保护可以通过四烷基氟化胺来脱去。SEM醚对分解四氢吡喃基(THP) 和叔丁基二甲基硅醚（TBS）的酸性条件（AcOH-H2O,THF, 45℃, 7 小时）是稳定的。

SEM-Cl(TMSCH2CH2OCH2-)保护羟基示例

    Exposure of an alcohol 1 in CH2Cl2 (ca, 2M) under an inert atmosphere containing 4-5 eq. of DIEA, to SEMCl (ca, 3 eq) at 25-40oC,affords the SEM ether in high yield.

SEM 保护基脱保护示例

     Removed of the SEM can be accomplished via reaction with Bu4NF (at concentration > 2M) in dry THF at 45oC. Standard extractive workup followed by rough SiO2 filtration give the desired product.