Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors

Chemistry, an Asian Journal
Mukta Shaw, Amit Kumar

Abstract

Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields and regenerate easily separable and reusable phenylpropiolic acid. Deoxy-PPGs containing armed and disarmed groups survived well under the optimized reaction conditions. In addition, the orthogonal nature of D-PPGs was showcased, and 1,1'-linked trehalose-type sugar was also synthesized.

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