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Issue 42, 2014
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Synthesis of L-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors

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Abstract

Herein we describe the synthesis of a series of novel fused bicyclic 1,2,3-triazoles from commercially available, natural deoxy sugar, L-rhamnose. The key reactions involved are (i) Zn(OTf)2 catalyzed enantioselective alkynylation of L-rhamnose derived azidoaldehyde and (ii) deprotection of the acid sensitive 1,2-isopropylidene group followed by in situ intramolecular click-cycloaddition of azidoalkynols. Some compounds exhibit excellent sodium-glucose transporter (SGLT1 and SGLT2) inhibition activity.

Graphical abstract: Synthesis of l-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors

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Publication details

The article was received on 25 Jun 2014, accepted on 08 Aug 2014 and first published on 08 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01319K
Citation: Org. Biomol. Chem., 2014,12, 8415-8421
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    Synthesis of L-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors

    S. R. Putapatri, A. Kanwal, B. Sridhar, S. K. Banerjee and S. Kantevari, Org. Biomol. Chem., 2014, 12, 8415
    DOI: 10.1039/C4OB01319K

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