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

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Abstract:

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.

Keywords: base-sensitive; dna/rna chemical synthesis; n-protected nucleosides; teoc group

Document Type: Review Article

DOI: https://doi.org/10.2174/1570178043488419

Affiliations: CREST, JST (Japan Science and Technology Agency), Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.

Publication date: 2004-04-01

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