Synthesis of α-Azido aldehydes. Stereoselective access to a protected lincosamine analogue

Article abstract of DOI:10.1016/S0040-4020(97)00240-8

Reaction of ketone 3 with dichloromethyllithium gave a unique branched-chain dichloromethyl sugar 7 whose structure was ascertained by X-ray crystallography. Transformation of 7 in seven steps, involving the key-intermediate α-azido-aldehyde 9, afforded the protected lincosamine analogue 14.