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Silicon-Assisted Ferrier Rearrangement in Preparation of C3-Silyl Glycosides
Pradip Das1, Satya Ravi Teja Miriyala1,2, D Srinivasa Reddy1,2
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Abstract:
Herein, we report a Lewis acid catalyzed Ferrier rearrangement glycosylation strategy using the α-effect of C3-silylated glucal donors. The dimethylphenylsilyl group at the C3 position promotes the reaction where the unactivated free hydroxy group at the C3 position acts as a leaving group. An inexpensive 5 mol % loading of AlCl3 was employed as the catalyst to achieve the desired transformation. This work provides the first efficient access to C3-silyl glycosides. Further, diversification of the obtained products is achieved through modified Fleming-Tamao oxidation and olefin functionalization.
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