Synthesis of oxepines and 2-branched pyranosides from a d-glucal-derived gem-dibromo-1,2-cyclopropanated sugar.
The conversion of cyclopropane-fused carbohydrates into oxepines is an attractive method for accessing diverse members of the septanoside family of carbohydrate mimetics. 2-Bromooxepines are obtained through silver(I)-promoted thermal ring expansion of a d-glucal-derived gem-dihalocyclopropanated sugar. In contrast, cyclopropane ring cleavage under basic conditions leads to 2-C-branched pyranosides, not the 2-bromooxepine structures assigned in an earlier report.
Hewitt
Russell J
RJ
School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand.
Harvey
Joanne E
JE
D002241:Carbohydrates / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002241:Carbohydrates; D003521:Cyclopropanes; D004852:Epoxy Compounds; D010082:Oxepins; C001289:d-glucal; D003847:Deoxyglucose