Issue 12, 1997

Synthesis of 2-substituted 2′-deoxyguanosines and 6-O-allylguanines via the activation of C-2 by a trifluoromethanesulfonate group

Abstract

A new general synthesis of 2-substituted 2′-deoxyguanosine and 6-O-allylguanine analogues is reported. 2-O-Trifluoromethylsulfonyl-6-O-allyl-3′,5 ′-bis-O-(tert-butyldimethylsilyl)-2′- deoxyxanthosine 8 can be converted into a 2-substituted 2′-deoxyguanosine analogue by substitution of the triflate (trifluoromethanesulfonate) moiety using a selected nucleophile, followed by deprotection. Therefore, a 2′-deoxyguanosine may overall be converted into a 2-substituted 2′-hypoxanthosine analogue in seven steps. Similar methodology has been used to synthesize 2-substituted 6-O-allylguanines which are of particular interest as potential resistance-modifying agents in cancer chemotherapy.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1997, 1887-1894

Synthesis of 2-substituted 2′-deoxyguanosines and 6-O-allylguanines via the activation of C-2 by a trifluoromethanesulfonate group

C. Edwards, G. Boche, T. Steinbrecher and S. Scheer, J. Chem. Soc., Perkin Trans. 1, 1997, 1887 DOI: 10.1039/A604559F

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