A General Method for the Synthesis of Cyclodextrinyl Aldehydes and Carboxylic Acids

Juyoung Yoon, Sungyeap Hong, Kristy A. Martin, Anthony W. Czarnik

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52 Scopus citations

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 languageEnglish
Pages (from-to)2792-2795
Number of pages4
JournalJournal of Organic Chemistry
Volume60
Issue number9
DOIs
StatePublished - 1 May 1995

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