Synthesis of some 2-O-(2-hydroxyalkyl) and 2-O-(2,3-dihydroxyalkyl) derivatives of cyclomaltoheptaose

Article abstract of DOI:10.1016/0008-6215(91)89010-D

On alkylation of cyclomaltoheptaose with oxiranes, promoted by alkali of low concentration, substitution at secondary positions, particularly at O-2, is favoured.The reaction has been used to prepare the 2-O-<(R)- and (S)-2-hydroxypropyl>, 2-O-(2-hydroxy-2-methylpropyl), 2-O-<(R)- and (S)-2,3-dihydroxypropyl>, and 2-O-<(R)- and (S)-2,3-dihydroxy-2-methylpropyl)derivatives.Each of these derivatives is less soluble in water than cyclomaltoheptaose, and their complexes with toluene, in contrast to that of cyclomaltoheptaose, are well soluble in water.