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Selective modification of mono-altro-β-cyclodextrin: dependence of O-sulfonylation position on the shape of sulfonylating reactant

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
17
Identifiers
DOI: 10.1016/j.tetlet.2004.03.018
Keywords
  • Cyclodextrin
  • Altroside
  • Modification
  • Sulfonylation

Abstract

Abstract Mono- altro-β-cyclodextrin, which has 21 different hydroxyl groups, was selectively sulfonylated by 2-naphthalenesulfonyl chloride at the 2 A-OH of the altrose residue. By using 1-naphthalenesulfonyl chloride as reactant, the 3 G-OH of the neighboring glucose became available for selective sulfonylation, and the resulted sulfonate was proved to be a very important intermediate for introducing functionalities to the saccharide adjacent to the altroside of mono- altro-β-cyclodextrin that is capable of controlling the orientation of substrate.

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