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

Document Type: Review Article

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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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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