Total synthesis of pseudouridine via Heck-type C-glycosylation??
New Journal of Chemistry Pub Date: 2019-05-06 DOI: 10.1039/C9NJ01012B
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).
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Journal Name：New Journal of Chemistry
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CAS no.: 89640-58-4
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