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A series of hydroxymethyl branched analogues of antiviral apio d4Ns was synthesized from D-arabinose. The SN2' ring opening reaction of 2,2'-anhydro-alpha-D-pyrimidinenucleoside (10) was mainly investigated. The reaction selectively gave SN2' adducts, which were deprotected to furnish the desired alpha-D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides (2).

Synthesis and antiviral evaluation of -D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides