Synthesis of 5-chloro-1-(2,3-dideoxy-3-fluoro-beta-D-glycero-hex-2- enopyranose-4-ulosyl)uracil as potential anticancer/antiviral agent.
Peracetylated alpha-D-glucose was coupled with silylated 5-chlorouracil. The product (2) was deacetylated and 4',6'-hydroxyls were then protected with 4',6'-O-isopropylidene group. Fluorine was introduced at the 3'-position, followed by acetylation, deprotection, tritylation, oxidation and deritylation of subsequent compounds gave the target compound (10).
Khan
A R
AR
Department of Chemistry, Florida A & M University, Tallahassee, Florida 32307, USA.
Mulligan
K X
KX
Ollapally
A P
AP
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
C442708:5-chloro-1-(2,3-dideoxy-3-fluoro-glycero-hex-2- enopyranose-4-ulosyl)uracil; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D014498:Uracil