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Issue 18, 1997
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Protection of the guanine residue during synthesis of2′-O-alkylguanosine derivatives

Abstract

Highly selective 2′-O-alkylation of 3′,5′-O-(tetraisopropyldisiloxane-1,3-diyl) guanosine has been achieved by using an alkyl halide and a sterically hindered strong organic base, when the 6-O atom is protected with either a 2-nitrophenyl or a tert-butyldiphenylsilyl group prior to the alkylation. A minimum of chromatography is required, the yields are high and none of the unwanted isomer is produced. Moreover, the highly versatile intermediates enable the synthesis of several new 2′-O-alkylguanosine derivatives as well as base-modified analogues.

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Article type: Paper
DOI: 10.1039/A700813I
Citation: J. Chem. Soc., Perkin Trans. 1, 1997,0, 2779-2788
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    Protection of the guanine residue during synthesis of 2′-O-alkylguanosine derivatives

    M. Grøtli, M. Douglas, B. Beijer, R. Güimil García, R. Eritja and B. Sproat, J. Chem. Soc., Perkin Trans. 1, 1997, 0, 2779
    DOI: 10.1039/A700813I

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