472968-87-9Relevant academic research and scientific papers
A practical stereoselective synthesis and novel cocrystallizations of an amphiphatic SGLT-2 inhibitor
Deshpande, Prashant P.,Singh, Janak,Pullockaran, Annie,Kissick, Thomas,Ellsworth, Bruce A.,Gougoutas, Jack Z.,Dimarco, John,Fakes, Michael,Reyes, Mayra,Lai, Chiajen,Lobinger, Hidegard,Denzel, Theo,Ermann, Peter,Crispino, Gerard,Randazzo, Michael,Gao, Zenrong,Randazzo, Renee,Lindrud, Mark,Rosso, Victor,Buono, Frederic,Doubleday, Wendel W.,Leung, Simon,Richberg, Pricilla,Hughes, David,Washburn, William N.,Meng, Wei,Volk, Kevin J.,Mueller, Richard H.
experimental part, p. 577 - 585 (2012/08/07)
A practical synthesis of the SGLT-2 inhibitor β-C-aryl-d-glucoside (1) has been developed. The route employed 2,3,4,6-tetra-O-trimethlysilyl-d- glucano-1,5-lactone as the key chiral building block, prepared efficiently from the commercially available, inexpensive raw materials, d-gluconolactone and trimethylsilyl chloride. The salient step in the synthesis is the Lewis acid-mediated stereoselective reduction of a methyl C-aryl peracetylated glycoside using a silyl hydride to set the stereochemistry of the crucial anomeric chiral center. Several novel cocrystalline complexes of 1 with l-phenylalanine and l-proline were discovered. Single-crystal structures of these complexes and several synthetic intermediates have been determined. The l-phenylalanine complex was developed and used to purify and isolate the API. All steps were implemented at multikilogram scale.
Methods of producing C-aryl glucoside SGLT2 inhibitors
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Page 17, (2010/02/07)
Method for the production of C-aryl glucoside SGLT2 inhibitors useful for the treatment of diabetes and related diseases. and intermediates thereof. The C-aryl glucosides may be complexed with amino acid complex forming reagents.
