Synthesis of alpha-fluorosulfonate and alpha-fluorosulfonamide analogues of a sulfated carbohydrate.
The first synthesis of sulfonamide and sulfonate analogues of a sulfated carbohydrate in which the ester oxygen of the sulfate is replaced with a CHF or CF2 group is reported. This was accomplished by electrophilic fluorination of the protected sulfonate and sulfonamide precursors. [reaction: see text].
Navidpour
Latifeh
L
Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario, Canada N2L 3G1.
Lu
Wallach
W
Taylor
Scott D
SD
D001965:Bromides / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005459:Fluorides / Q000138:chemical synthesis*; D018020:Lithium Compounds / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010100:Oxygen / Q000737:chemistry; D013431:Sulfates / Q000737:chemistry; D013464:Sulfuric Acids / Q000138:chemical synthesis*
D001965:Bromides; D002241:Carbohydrates; D004952:Esters; D018020:Lithium Compounds; D013431:Sulfates; D013464:Sulfuric Acids; C040949:lithium bromide; C046106:fluorosulfonic acid; D005459:Fluorides; D010100:Oxygen