O. Schulze, S. Bruns, J. Voss
Dec 1, 2000
Citations
0
Influential Citations
8
Citations
Journal
Carbohydrate research
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.