• Bulletin of the Korean Chemical Society
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• v.30 no.9
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• pp.2043-2050
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• 2009

2′-$\beta$-C-Methylneplanocin A (3) was synthesized via 2-$\beta$-C-methylribonolactone, prepared by a modified Whistler and BeMiller’s method developed by our laboratory, as potential anti-HCV agent. Reduction of 14 with Dibal-H afforded 26 in a good yield with a trace of 25, whereas a Luche reduction gave 26/25 = 4/1 mixture. Several attempts were made to chemoselectively remove TBS group in the presence of TBDPS group and treatment with both PPTS and TsOH showed the best result. Condensation of 26 with 6-chloropurine under Mitsunobu conditions produced an $S_N$2 product 27 along with an $S_N$2′ product 28.