Synthesis of 2‐deoxy sugars
The reduction of acetylated or benzoylated glycosyl halides or selenides with low concentrations of tributylstannane leads to 2-deoxy sugars. An important step in this radical-chain reaction is the cis-selective migration of an ester group. The broad applicability of this method is demonstrated by the synthesis of mono- and dideoxy sugars, of α- and β-deoxy sugars, of deoxypyranoses and deoxyfuranoses, of deoxypentosyl- and -hexosyl carbohydrates.