Abstract
Protected 6- C-sulfosugars have been transformed into alkyl sulfonates and N-alkylsulfonamides, including a pseudo-disaccharide with a 6 to 6′-sulfonamide linkage. The method involves the oxidation of 6-thioacetate sugar derivatives to 6- C-sulfosugars, and their transformation into sulfonyl chlorides using SO 2Cl 2 in anhydrous CH 2Cl 2 followed by in situ coupling with nucleophiles in the presence of an excess of base. Sulfonylation through phase-transfer conditions has proved to be suitable for the synthesis of the pseudo-disaccharide.
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