A click chemistry approach to the synthesis of 3′-deoxy-2′-substituted carbanucleoside precursors

We report herein the synthesis of various carbanucleoside precursors by a click chemistry approach, employing cyclopent-3-en-1-ylmethanol 1 as starting material. Using aziridine (±)-2 as key intermediate, we describe an efficient procedure for the synthesis of a series of 3′-deoxy-2′-substituted carbanucleoside precursors, namely aminoalcohols of type (±)-3. Alternatively, transformation of alcohol 1 into (3-azido-4-halo-1-cyclopentyl)methanols of type (±)-4, allows the preparation of 1,2,3-triazole carbanucleoside analogues of types (±)-5 and (±)-8.

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