1998 carbohydrates

carbohydratesU 0500

26 - 244Novel Method to Prepare Dihydroxy Permethylated β-CyclodextrinIsomeric Intermediates for Bifunctional Enzyme Mimics. — Dihy-droxy permethylated β-cyclodextrins are prepared from natural β-cyclodextrin,following a convenient three-step process. Treatment with 3.5 equivalents ofTbs-Cl and subsequent methylation of all remaining hydroxy groups with alarge excess of NaH and Me-I is followed by desilylation with NH4F to give amixture of three regioisomeric title compounds, which are separated by columnchromatography. These diols are used as nucleophiles or are transformed todimesylates, which are of interest for further functionalization. — (CHEN, Z.;BRADSHAW, J. S.; SHEN, Y.-F.; HABATA, Y.; LEE, M. L.; J. Org. Chem.62 (1997) 24, 8529-8534; Dep. Chem. Biochem., Brigham Young Univ., Provo,UT 84602, USA; EN)

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