Activation of glycosyl methylpropiolates by TfOH.

Activation of glycosyl methylpropiolates by TfOH was investigated. Armed and superarmed glycosyl donors can be activated by use of 0.2 equivalent TfOH whereas 1.0 equivalent of TfOH was required for the activation of the disarmed glycosyl donors. All the glycosidations gave very good yields. The method is suitable for synthesis of glycosides and disaccharides and it may result in the hydrolysis of the interglycosidic bond if the sugar at the non-reducing end is armed or superarmed. These problems are not seen when gold-catalyzed activation procedures are invoked for the activation of glycosyl alkynoates. Copyright © 2024 Elsevier Ltd. All rights reserved.

Citation

Gulab Walke, Niteshlal Kasdekar, Soumyaranjan Pati, Marc Taillefer, Florian Jaroschik, Srinivas Hotha. Activation of glycosyl methylpropiolates by TfOH. Carbohydrate research. 2024 May;539:109106

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PMID: 38640704

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