Synthesis of C7-C16-alkyl maltosides in the presence of tin(IV) chloride as a Lewis acid catalyst

Abstract

The synthesis of C7- to C16-alkyl maltosides in the presence of tin(IV) chloride as Lewis acid catalyst was performed. The characterization of the products and theoretical investigation of the crucial step in the synthesis were carried out.  The preparation of the β-maltosides required reaction time of 1 h, and that of the α-maltosides was 72 h. The side products were the α-D-maltosidechloride and 2-hydroxy-β-maltoside, respectively. The PM3 calculation confirmed the formation of the kinetically controlled β-product.

KEY WORDS: Maltose, Synthesis of maltosides, Tin(IV) chloride, PM3

Bull. Chem. Soc. Ethiop. 2011, 25(1), 83-90.