Abstract
A new method for the synthesis of α‐2‐deoxyglycosides from hex‐1‐en‐3‐uloses is reported. Several acids were surveyed for their ability to mediate the conjugate addition of cyclohexanol to a glucal derived α,β‐unsaturated ketone. Although several acids successfully afforded the α‐2‐deoxy‐3‐uloside as a single anomer, Ph3P · HBr in benzene afforded the highest yield of product. These conditions were then applied to other alcohol nucleophiles, and it was found that nonsterically hindered alcohols readily undergo conjugate addition. Finally, the stereoselectivity of reduction of the resulting α‐2‐deoxy‐3‐uloside was determined for several hydride‐reducing agents.
Published Version
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call