Lewis acid deprotection of silyl-protected oligonucleotides and base-sensitive oligonucleotide analogues

Oligonucleotides protected with N-(trimethylsilylethoxycarbonyl) (Teoc) and P-(trimethylsilylethanol) (Tse) groups were synthesized and deprotected by a single ZnBr2 treatment. Teoc group stabilized dA against depurination. This strategy was applied to the synthesis of base-sensitive oligonucleotide prodrugs bearing S-acetyl-2-thioethyl (Sate) phosphotriesters.