Synthesis of 1,2-unsaturated pyranosylphosphonate nucleosides from 3,4,6-tri-O-acetyl-D-glycal.
Ferrier rearrangement of 3,4,6-tri-O-acetyl-D-glucal (1) in the presence of triethylphosphite afforded the 2,3-unsaturated pyranose 2. Deacetylation and simultaneous migration of the double bond to 1,2-position in the sugar moiety was achieved by stirring in sodium ethoxide. Tosylation with one equivalent of tosyl chloride afforded 4. Nucleophile displacement of the tosylate of 4 with nucleobase in the presence of NaH/DMF followed by deprotection gave the desired 1,2-unsaturated pyranosylphosphonates 7a-c.
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Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Koom, Egypt.
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D002241:Carbohydrates / Q000737:chemistry; D003640:Dealkylation; D003847:Deoxyglucose / Q000031:analogs & derivatives / Q000737:chemistry*; D007202:Indicators and Reagents; D009705:Nucleosides / Q000138:chemical synthesis*; D017905:Phosphites; D014105:Tosyl Compounds / Q000737:chemistry
D002241:Carbohydrates; D007202:Indicators and Reagents; D009705:Nucleosides; D017905:Phosphites; D014105:Tosyl Compounds; C025506:4-toluenesulfonyl chloride; C043334:3,4,6-tri-O-acetylglucal; C018680:triethyl phosphite; D003847:Deoxyglucose