Synthesis of N-(Trimethylsilylethoxycarbonyl)-deoxycytidine and Deoxyadenosine Derivatives as Key Intermediates for the DNA Synthesis using Fluoride Ion-Promoted Deprotection Strategy

An improved method for the synthesis of trimethylsilylethyl chloroformate (Teoc-Cl) was studied in great detail. N-Teoc-adenosine, N-Teoccytidine and their deoxyribonucleoside derivatives were synthesized as the key synthetic intermediates for the synthesis of base-sensitive oligonucleotide derivatives by use of N-methylimidazole. The stability and chemical properties of these Nprotected nucleoside derivatives were examined.