Synthesis of novel 6-substituted thymine ribonucleosides and their 3′-fluorinated analogues

Add time:07/23/2019    Source:sciencedirect.com

Nine novel 6-fluorothymine nucleoside analogues of both N(1)-α/β and N(3)-β-ribo series were prepared by the Vorbrüggen method starting from persilylated 6-fluorothymine and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose, 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-α,β-d-ribofuranose or 1,2,3,5-tetra-O-benzoyl-β-d-ribofuranose and its α-anomer. Protected N(3)-β-d-ribofuranosides were prepared as sole products in high yields at room temperature. A mixture of benzoylated N(1)-β- and α-anomeric ribonucleosides was obtained at lower temperatures. Yields of β-anomers and stereoselectivities (β:α=2.2/4.5:1) of the condensation reactions depended on reaction conditions and the structure of the glycosylating agent. Debenzoylation of 6-fluorothymine N(1)- or N(3)-β-d-ribofuranosides and their 3′-fluorodeoxy analogues by LiOH monohydrate in MeCN/H2O resulted in the corresponding fluorinated nucleosides in good yields, whereas the deprotection of N(1)-α-ribofuranosides under the same conditions unexpectedly yielded 6,2′-O-α-d-anhydronucleosides. 6-Substituted (OMe, NH2) thymine β-ribonucleosides were prepared by the treatment of protected N(1)-β-d-ribosides with nucleophilic agents.

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