Synthesis of some 2-O-(2-hydroxyalkyl) and 2-O-(2,3-dihydroxyalkyl) derivatives of cyclomaltoheptaose.
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.
Lindberg
B
B
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Lindberg
J
J
Pitha
J
J
Rao
C T
CT
Harata
K
K
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008969:Molecular Sequence Data; D013329:Structure-Activity Relationship; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D007202:Indicators and Reagents; D047392:beta-Cyclodextrins; C031215:betadex