-2–6-[4-chloro-3-phenyl]tetrahydro-2H-pyran-3,4,5-triyl triacetate
-2–6-[4-chloro-3-phenyl]tetrahydro-2H-pyran-3,4,5-triyl triacetate (CAS: 461432-25-7) is a protected glucose-derived intermediate featuring a chlorinated aromatic aglycone and acetyl-protected hydroxyl groups on the pyranose ring. This compound represents a key intermediate in the synthesis of C-glycoside pharmaceutical ingredients, most notably the SGLT2 inhibitor class of antidiabetic drugs. The acetate protecting groups stabilize the sugar moiety during synthetic transformations and are readily removed under mild basic conditions when deprotection is required. The chloroaryl substituent provides the lipophilic pharmacophore characteristic of gliflozin drugs, while the tetrahydropyran core maintains the glucose-mimicking structure essential for sodium-glucose cotransporter binding. Manufactured under stringent quality controls to ensure stereochemical purity and low impurity levels, this intermediate supports efficient multi-step assembly of high-value pharmaceutical actives for metabolic disease treatment.
– SGLT2 Inhibitor Synthesis: Serves as a key protected intermediate in the manufacture of gliflozin-class antidiabetic drugs including empagliflozin and related actives.
– C-Glycoside Construction: Used in building carbon-linked glycosides that resist enzymatic hydrolysis for enhanced metabolic stability.
– Pharmaceutical Process Development: Applied in process research and scale-up for C-glycoside APIs requiring stereochemically pure pyranose intermediates.
– Protected Sugar Chemistry: The acetyl groups enable selective synthetic transformations before mild deprotection reveals the free hydroxyls.
Product Name: -2–6-[4-chloro-3-phenyl]tetrahydro-2H-pyran-3,4,5-triyl triacetate
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