Convenient preparation of 3,5-anhydro- and 2,5-anhydropentofuranosides, and 5,6-anhydro-d-glucofuranose by use of the Mitsunobu reaction

Add time:09/07/2019    Source:sciencedirect.com

Methyl 3,5-anhydro-α-d-xylofuranosides are obtained by use of the Mitsunobu reaction from 2-O-protected methyl α-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-α-d- and 2,3-anhydro-α-l-lyxofuranosides by nucleophilic ring opening, yields the corresponding methyl 2,5-anhydro-α-d- and 2,5-anhydro-α-l-arabinofuranosides. Ring opening of 3,5-anhydro-1,2-O-isopropylidene-α-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-α-d-glucofuranose is formed by the Mitsunobu reaction of 1,2-O-isopropylidene-α-d-glucofuranose. Its structure is verified by single-crystal X-ray diffraction analysis.

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