Efficient route to 2-deoxy beta-O-aryl-d-glycosides via direct displacement of glycosyl iodides.
[reaction: see text]. The conversion of glycals to 2-deoxy glycosyl acetates followed by reaction with trimethylsilyl iodide affords the corresponding glycosyl iodides, which readily undergo substitution with aryl alkoxy anions to provide 2-deoxy-beta-O-aryl glycosides. Direct displacement of the anomeric iodide alleviates the need to introduce temporary C-2 stereodirecting groups that require subsequent removal. The only observable byproducts from the glycosylations result from elimination of HI giving the starting glycals, which can be recycled through the reaction sequence.
Department of Chemistry, University of California, Davis, One Shields Ave., Davis, California 95616, USA.
Son N
SN
Lam
Jacquelyn
J
Gervay-Hague
D002236:Carbohydrate Conformation; D003837:Deoxy Sugars / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D003837:Deoxy Sugars; D006027:Glycosides; D006841:Hydrocarbons, Aromatic; D006847:Hydrocarbons, Iodinated; D014297:Trimethylsilyl Compounds; C419804:trimethylsilyl iodide