Issue 42, 2014
From the journal:

Organic & Biomolecular Chemistry

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

Siddamal Reddy Putapatri,a   Abhinav Kanwal,b   Balasubramanian Sridhar,c   Sanjay K. Banerjee*b  and  Srinivas Kantevari*a  

* Corresponding authors

a Organic Chemistry Division-II (C P C Division), CSIR-Indian Institute of Chemical Technology, Hyderabad, India
E-mail: kantevari@yahoo.com, kantevari@gmail.com
Fax: +91-40-27198933
Tel: +91-40-27191438

b Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, India
E-mail: banerjees74@hotmail.com

c Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad, India

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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DOI
https://doi.org/10.1039/C4OB01319K
Article type
Paper
Submitted
25 Jun 2014
Accepted
08 Aug 2014
First published
08 Aug 2014

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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