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We describe an efficient and stereoselective synthesis of 1'-substituted-β-carbocylic nucleosides 5 via gem-dichlorooxirane intermediate 7, which directly condensed with weak nucleophiles such as pyrimidines or purines. The formation of gem-dichlorooxirane 7 and direct nucleobase condensation exclusively proceeded in protic polar solvents like MeOH. This method provides a general and modular route for the late-stage diversification of 1'-modified nucleosides.
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