Abstract
The selective synthesis of the primary-side monoaldehyde of β-cyclodextrin, 6-deoxy-6-formyl-β-cyclodextrin, was accomplished by oxidation of the corresponding tosylate utilizing the Nace reaction (DMSO/collidine). This monoaldehyde was then used as the starting material in several reactions including reduction, addition of NaHSO3, addition of the a-nucleophiles hydroxylamine and hydrazine, and reductive amination. Of particular interest is the conversion of the monoaldehyde to the primary side carboxylic acid, 6-deoxy-6-carboxy-β-cyclodextrin, via bromine oxidation. This general method sequence can be applied to any tosyl derivative of cyclodextrin as demonstrated in the synthesis of β-cyclodextrin-A,D-dialdehyde and β-cyclodextrin-A,D-diacid.
Original language | English |
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Pages (from-to) | 2792-2795 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 60 |
Issue number | 9 |
DOIs | |
State | Published - 1 May 1995 |