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  • Title: The thio-Mitsunobu reaction of D-glucitol, D-mannitol, galactitol and 1-seleno-D-xylitol.
    Author: Schulze O, Bruns S, Voss J, Adiwidjaja G.
    Journal: Carbohydr Res; 2000 Dec 01; 329(4):781-90. PubMed ID: 11125820.
    Abstract:
    Unprotected D-glucitol is transformed into 5-O-acetyl-1,4-anhydro-6-thio-D-glucitol (3) in one step by use of the thio-Mitsunobu reaction. Rearrangement (acetyl group migration) to form 3-O-acetyl-1,4-anhydro-6-thio-D-glucitol occurs during column chromatography of 3 on silica gel. 2,5-Di-O-acetyl-1,6-dithio-D-mannitol and 1,6-di-S-acetyl-2,5-anhydro-1,6-dithio-D-glucitol (characterized as the corresponding p-nitrobenzoates) are formed from D-mannitol, whereas galactitol yields a mass of unidentified products. 1-Seleno-D-xylitol, produced by reduction of D-xylose with hydrogen selenide, does not undergo a Mitsunobu reaction.
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