The thio-Mitsunobu reaction of D-glucitol, D-mannitol, galactitol and 1-seleno-D-xylitol.
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.
Schulze
O
O
Institut für Organische Chemie der Universität Hamburg, Germany.
Bruns
S
S
Voss
J
J
Adiwidjaja
G
G
D002850:Chromatography, Gel; D004376:Galactitol / Q000737:chemistry*; D008353:Mannitol / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013012:Sorbitol / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry; D014993:Xylitol / Q000031:analogs & derivatives* / Q000737:chemistry*
D013457:Sulfur Compounds; D004376:Galactitol; D008353:Mannitol; D013012:Sorbitol; D014993:Xylitol