Regioselective Synthesis of 6-Alkynyl-6-Deoxy and Pseudo-C-Disaccharides Derivatives of Mannofuranose via a 5,6-Cyclic Sulfate

Thierry Gourlain; Anne Wadouachi; Daniel Beaupère

doi:10.1055/s-1999-3389

Synthesis 1999; 1999(2): 290-294
DOI: 10.1055/s-1999-3389

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Regioselective Synthesis of 6-Alkynyl-6-Deoxy and Pseudo-C-Disaccharides Derivatives of Mannofuranose via a 5,6-Cyclic Sulfate

Thierry Gourlain^* , Anne Wadouachi, Daniel Beaupère

^*Laboratoire de Chimie Organique, Université de Picardie Jules Verne, 33 rue Saint-Leu F-80039 Amiens, France; Fax +33(3)22 82 75 62; E-mail: daniel.Beaupère@sc.u-picardie.fr

Abstract

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C-6 opening of a 5,6-cyclic sulfate derivative of mannofuranoside 1 with acetylenic anion generated from oct-1-yne or phenylethyne gave corresponding 6-alkynyl-6-deoxy derivatives 2 and 3 respectively. The reaction of 5,6-cyclic sulfate 1 with lithium acetylide derived from monosaccharide led to pseudo-C-disaccharide 5. A one-pot procedure was achieved using lithium acetylide in THF/HMPA, to prepare symmetric pseudo-C-disaccharide 7. This method, used with a 5,6-cyclic sulfate derivative of glucofuranose 11 with the acetylide anion derived from mannofuranose 9, gave the corresponding nonsymmetric pseudo-C-disaccharide 13.

cyclic sulfate - monosaccharides - alkynes - 6-alkynyl sugars - pseudo-C-disaccharides

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