Abstract
An efficient and scalable synthesis of an antidiabetic drug, tofogliflozin (1), which was identified as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor, is described. A key factor in the synthesis of 1 was the selection of the purpose-designed protecting group, which plays a strategic role in protection, chemoselective activation, and crystalline purification. The developed and optimized method made it possible to prepare 1 on a multidecagram scale without any column chromatography.
MeSH terms
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Benzhydryl Compounds / chemical synthesis*
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Benzhydryl Compounds / chemistry
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Glucose / chemistry*
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Glucosides / chemical synthesis*
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Glucosides / chemistry
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Molecular Structure
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Sodium-Glucose Transporter 2 / chemistry*
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Sodium-Glucose Transporter 2 Inhibitors*
Substances
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Benzhydryl Compounds
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Glucosides
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SLC5A2 protein, human
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Sodium-Glucose Transporter 2
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Sodium-Glucose Transporter 2 Inhibitors
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Glucose
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6-((4-ethylphenyl)methyl)-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)spiro(isobenzofuran-1(3H),2'-(2H)pyran)-3',4',5'-triol