Carbohydrate research

The thio-Mitsunobu reaction: a useful tool for the preparation of 2, 5-anhydro-2-thio-and 3, 5-anhydro-3-thiopentofuranosides

O Schulze, J Voss, G Adiwidjaja, F Olbrich

Index: Schulze, Oliver; Voss, Juergen; Adiwidjaja, Gunadi; Olbrich, Falk Carbohydrate Research, 2004 , vol. 339, # 10 p. 1787 - 1802

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Citation Number: 13

Abstract

The unprotected methyl l-arabinofuranosides, d-ribofuranosides and d-xylofuranosides are transformed into the corresponding S-acetyl-5-thio derivatives by the thio-Mitsunobu reaction. Mesylation and subsequent reaction with sodium hydrogen carbonate led, depending on the configuration of the intermediate, to 2, 5-anhydro-2-thio-or 3, 5-anhydro-3- thiopentofuranosides. Due to inversion at C-3 or C-2 during the intramolecular ...