A d-ribose-derived α-amino nitrile as a versatile intermediate for the collective synthesis of piperidine-type iminosugar C-glycosides

Iminosugar C-glycosides are valuable entities in medicinal chemistry. Herein we disclose a collective synthesis approach to such compounds, in a route that features a remarkably stable, fully characterised, ribose-derived iminium salt as a key intermediate. Addition of organometallic reagents to this key intermediate delivers a variety of iminosugar C-glycoside products in high yields and with excellent stereocontrol.