2021 Volume 79 Issue 6 Pages 532-546
Recently, sodium glucose cotransporter 2 (SGLT2) inhibitors have been received a lot of attention for the treatment of diabetes. C-arylglucoside compounds have been shown to be potent SGLT2 inhibition. Reports on the synthesis of SGLT2 inhibitors have appeared. Several reviews have also been reported as so far. This review deals with SGLT2 inhibitors approved by 2019 and the synthetic methods of some of these compounds, which have appeared in academic journals, from view point of synthetic strategy. The reactions of several kind of sugar electrophiles with aryl carbanions generated from aryl halides by the halogen-metal exchange reactions have met success to form the desired carbon-carbon bond. Lactone derivatives, anhydro-sugars and glycosyl halides have been used as sugar electrophiles. More recently, by use of α-oxo-vinylsulfone, cross-coupling with aryl boronate have been proven to afford C-aryl glycal leading to C-glucoside. Construction of aromatic ring by [4+2] cycloaddition of tetrahydropyran bearing dienone-yne under aerobic conditions has led to C-glucoside.
