Preparation of di-altro-β-cyclodextrins with two altrosides as the macrocyclic units through selective synthesis of regioisomers of di(2-O- mesitylenesulfonyl)-β-cyciodextrin

Article abstract of DOI:10.1248/cpb.45.631

Regioisomers of di(2-O-mesitylenesulfonyl)-β-cyclodextrin 2-4 were synthesized in 3, 4 times larger yields compared to those of the reported method using dibutyltin oxide/triethylamine/p-toluenesulfonyl chloride. Regio-isomers of di-mannoepoxy-β-cyclodextrin 5-7 were prepared from 2-4 and converted to the corresponding di-altro-β-cyclodextrins (8-10) with two altrosides as macrocyclic units, respectively. Conformations of the altrose parts of di-altro-β-cyclodextrins were investigated by NMR, and the altroside was found to change its conformation depending on whether or not it is a member of the macrocyclic ring and its position in the ring.

Full text of DOI:10.1248/cpb.45.631

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