Carbohydrate-2-deoxy-2-phosphonates: simple synthesis and Horner-Emmons reaction.
Phosphorus meets carbohydrates: Dimethyl phosphite reacts with ceric(IV) ammonium nitrate (CAN) to give phosphonyl radicals that add to glycals 1. The derivatives 2 were isolated in high yields and during a subsequent Horner-Emmons reaction underwent an interesting elimination to give 3,6-dihydro-2H-pyrans 3. The short sequence with simple precursors is applicable to the transformation of hexoses, pentoses, and disaccharides. Bn = benzyl.
Elamparuthi
Elangovan
E
Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam, Germany.
Linker
Torsten
T
D002241:Carbohydrates / Q000737:chemistry*; D002563:Cerium / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D009566:Nitrates / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D002241:Carbohydrates; D005609:Free Radicals; D009566:Nitrates; D063065:Organophosphonates; D011714:Pyrans; D002563:Cerium; C006568:ammonium nitrate