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Updated: May 16, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Selective biocatalytic acylation studies on 5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine: an efficient synthesis of
Sunil K Singh1, L Chandrashekhar Reddy, Smriti Srivastava
1Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, India.
Abstract:
Lipozyme(®) TL IM (Theremomyces lanuginosus lipase immobilized on silica) in toluene catalyzes the acylation of the 2'-OH over the 3'-OH group in 5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine (5'-O-DMT-2',3'-secouridine) in a highly selective fashion in moderate to almost quantitative yields. The turn over during benzoyl transfer reactions mediated by vinyl benzoate or benzoic anhydride was faster than in acyl transfer reactions with vinyl acetate or C(1) to C(5) acid anhydrides; except in the case of butanoic anhydride. The 2'-O-benzoyl-5'-O-DMT-2',3'-secouridine obtained by Lipozyme(®) TL IM catalyzed benzoylation of 5'-O-DMT-2',3'-secouridine was successfully converted into its 3'-O-phosphoramidite derivative in satisfactory yield, which is a building block for the preparation of oligonucleotides containing the uracil monomer of UNA (unlocked nucleic acid).
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