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Synthesis 1992; 1992(11): 1129-1132
DOI: 10.1055/s-1992-26320
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Regioselective Tosylation of Aldonolactones

Inge Lundt* , Robert Madsen
  • *Department of Organic Chemistry, The Technical University of Denmark, Building 201, DK-2800 Lyngby, Denmark
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Publication Date:
17 September 2002 (online)

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An investigation of the selective di-O-acylation with p-toluenesulfonyl (tosyl) chloride of the four D-pentono-, the eight D-hexono-and D-glycero-D-gulo-heptonolactone has been undertaken, and a number of 2,5-, 2,6- and 2,7-di-O-tosylated lactones have been prepared. Monotosylation of L-erythrono- and L-rhamnonolactone gave the corresponding 2-O-tosylates.

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