Convenient preparation of 3,5-anhydro- and 2,5-anhydropentofuranosides, and 5,6-anhydro-D-glucofuranose by use of the Mitsunobu reaction.
Methyl 3,5-anhydro-alpha-D-xylofuranosides are obtained by use of the Mitsunobu reaction from 2-O-protected methyl alpha-D-xylofuranosides, which are easily prepared from D-xylose. The Mitsunobu reaction of methyl 3-N-benzylamino-3-deoxy- and 3-azido-3-deoxyarabinofuranosides, which are prepared from the conveniently available methyl 2,3-anhydro-alpha-D- and 2,3-anhydro-alpha-l-lyxofuranosides by nucleophilic ring opening, yields the corresponding methyl 2,5-anhydro-alpha-D- and 2,5-anhydro-alpha-l-arabinofuranosides. Ring opening of 3,5-anhydro-1,2-O-isopropylidene-alpha-D-xylofuranose with azide yields the corresponding 5-azido derivative. The structure and configuration of the products is confirmed by NMR spectroscopy. 5,6-Anhydro-1,2-O-isopropylidene-alpha-D-glucofuranose is formed by the Mitsunobu reaction of 1,2-O-isopropylidene-alpha-D-glucofuranose. Its structure is verified by single-crystal X-ray diffraction analysis.
Schulze
Oliver
O
Institut für Organische Chemie der Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany. olli@ukezyk.desy.de
Voss
Jürgen
J
Adiwidjaja
Gunadi
G
D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009904:Optical Rotation; D011725:Pyridines / Q000737:chemistry; D014994:Xylose / Q000737:chemistry
D005663:Furans; D011725:Pyridines; D014994:Xylose; D001089:Arabinose