Lindberg B, Lindberg J, Pitha J, Rao C T, Harata K
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Carbohydr Res. 1991 Dec 30;222:113-9. 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.
