Glycosylations of armed and disarmed trichloroacetimidate‐based glycosyl donors were carried out by using the AuCl3–phenylacetylene relay catalyst system. The effectiveness of this catalytic system was also compared with that of using AuCl3 alone as a catalyst. Glycosylations with these catalysts proceeded efficiently at room temperature within 5–45 min. Excellent diastereoselectivity was obtained for the glycosylation of 2‐O‐acetyl‐protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid‐sensitive nucleophiles such as Fmoc‐serine tert‐butyl ester or Fmoc‐threonine tert‐butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature.
A general strategy for the synthesis of analogues of radicamine B has been carried out from D-mannitol. This method has been further extended to the synthesis of analogues of codonopsine and codonopsinine using appropriate Grignard reagents. The hence obtained molecules have been tested against various commercially available glycosidases and found to act as moderate to good inhibitors.
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