TY - JOUR
T1 - Synthesis of l-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors
AU - Putapatri, Siddamal Reddy
AU - Kanwal, Abhinav
AU - Sridhar, Balasubramanian
AU - Banerjee, Sanjay K.
AU - Kantevari, Srinivas
PY - 2014/11/14
Y1 - 2014/11/14
N2 - 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. This journal is
AB - 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. This journal is
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U2 - 10.1039/c4ob01319k
DO - 10.1039/c4ob01319k
M3 - Article
C2 - 25175761
AN - SCOPUS:84908006510
SN - 1477-0520
VL - 12
SP - 8415
EP - 8421
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 42
ER -