Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

Add time:09/09/2019    Source:sciencedirect.com

Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3-benzyl-2-hydroxy-2-cyclopenten-1-one with an ee ⩾96%, using the tartaric ester/Ti(OiPr)4/t-BuOOH complex, and transformed to the corresponding 4′-substituted nucleoside analogues with up to 61% overall yield.

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