Synthesis of 2,3- or 1,2-unsaturated derivatives of 2-deoxy-2-trifluoromethylhexopyranoses.
The attempted conversion, by treatment with CsF/TBFA in MeCN, of acetylated derivatives of 2-chlorodifluoromethyl-2-deoxyhexopyranoses into their corresponding 2-trifluoromethyl derivatives was always accompanied by an elimination reaction. Thus, representative educts with the D-gluco- and D-manno-configuration gave derivatives of 2,3-dideoxy-2-trifluoromethyl-D-erythro-hex-2-enopyranose and 1,5-anhydro-2-deoxy-2-trifluoromethyl-d-arabino-hex-1-enitol, respectively. X-ray analyses are given for 1,3,4,6-tetra-O-acetyl-2-chlorodifluoromethyl-2-deoxy-alpha-D-mannopyranose and 4,6-di-O-acetyl-2,3-dideoxy-2-trifluoromethyl-alpha-D-erythro-hex-2-enopyranose.
Wegert
Anita
A
FB Chemie, Organische Chemie, Universität Rostock, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany.
Reinke
Helmut
H
Miethchen
Ralf
R
D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry*; D002845:Chromatography; D002855:Chromatography, Thin Layer; D003486:Cyanides / Q000737:chemistry*; D003837:Deoxy Sugars / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D006838:Hydrocarbons; D006859:Hydrogen; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D011714:Pyrans / Q000737:chemistry*; D014965:X-Rays
D002241:Carbohydrates; D003486:Cyanides; D003837:Deoxy Sugars; D005449:Fluorenes; D006027:Glycosides; D006838:Hydrocarbons; D011714:Pyrans; C030011:carbene; C041509:fluorene; D006859:Hydrogen; D008697:Methane