86448-01-3Relevant academic research and scientific papers
2-Deoxyglycosyl Fluorides in Oligosaccharide Synthesis
Juennemann, Josef,Lundt, Inge,Thiem, Joachim
, p. 759 - 764 (2007/10/02)
3,4-Di-O-acetyl-2,6-dibromo-2,6-dideoxy-α-D-mannopyranosyl fluoride (1) was treated with Lewis acid catalysts to give α-glycosides exclusively.Reactions with α- and β-glucosyl analogs yield α/β mixtures under the same conditions.With no assistance of anchimeric substituents at C-2 the stereoselectivity is directed by a glycosyl fluoride/catalyst/solvent complex.As shown in the 2-deoxy-arabino-hexopyranosyl series this leads to improved α/β ratios and yields. - Key Words: 2-Deoxyglycosides / Glycosylation, stereoselective / Glycosyl fluorides, 2-deoxy- / Lewis acid catalysis / Carbohydrates
