Stereoselective synthesis of a dioxa-bicyclo[3.2.1]octane SGLT2 inhibitor.
A promising class of SGLT2 inhibitors bearing a unique dioxa-bicyclo[3.2.1]octane motif was recently disclosed. An improved stereoselective synthesis providing efficient access to one of the most potent and selective compounds from this class is reported. A one-pot deprotection/cyclization was used as the key step to form the dioxa-bicyclo[3.2.1]octane motif with full control of stereochemistry. Using an appropriately substituted aryl group, the route enables the synthesis of any given compound from the class.
Pfizer Global Research and Development, Groton, Connecticut 06340, USA. vincent.mascitti@pfizer.com
Vincent
V
Mascitti
Cathy
C
Préville
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008968:Molecular Conformation; D000077203:Sodium-Glucose Transporter 2 Inhibitors; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D000077203:Sodium-Glucose Transporter 2 Inhibitors; C493209:dioxabicyclo(3.2.1)octane