Desfluoro Canagliflozin is a structurally related impurity of Canagliflozin, characterized by the absence of a 4-fluoro substituent on the phenyl ring of the parent compound. It retains the core sulfonamide-benzyl-fructofuranoside scaffold, featuring a 1,5-anhydro-1C-pentitol glycoside linked via a sulfur atom to a 4-chlorobenzoyl group. The removal of the fluorine atom alters the electronic distribution of the aromatic ring, potentially affecting metabolic stability. This compound arises as a synthetic byproduct during Canagliflozin production via defluorination pathways. It serves as a critical HPLC reference standard for quantifying process-related impurities in pharmaceutical development.
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InChI=1S/C24H26O5S/c1-14-7-8-16(24-23(28)22(27)21(26)19(13-25)29-24)11-17(14)12-18-9-10-20(30-18)15-5-3-2-4-6-15/h2-11,19,21-28H,12-13H2,1H3/t19-,21-,22+,23-,24+/m1/s1
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