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Total synthesis of pseudouridine via Heck-type C-glycosylation

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Abstract

The reaction of 2,4-dimethoxy-5-iodopyrimidine (8) and 3,5-di-O-tert-butyldimethylsilyl protected ribofuranoid glycal 4 was carried out with Pd(OAc)2 as the catalyst, PPh3 as the ligand and Et3N as the base in DMF at 70 °C followed by desilylation to afford exclusively the β-anomer of 5-(2,3-dideoxy-3-oxoribofuranosyl)-2,4-dimethoxypyrimidine (11) in a very good yield. The subsequent protecting group and functional group interconversions furnished pseudouridine (Ψ, 1).

Graphical abstract: Total synthesis of pseudouridine via Heck-type C-glycosylation

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Publication details

The article was received on 25 Feb 2019, accepted on 03 May 2019 and first published on 06 May 2019


Article type: Paper
DOI: 10.1039/C9NJ01012B
New J. Chem., 2019, Advance Article

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    Total synthesis of pseudouridine via Heck-type C-glycosylation

    C. Yu, H. Chang and T. Chien, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ01012B

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