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Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose

Hadžić Pavle (Faculty of Science, Institute of Chemistry, Novi Sad)
Vukojević Nada (Faculty of Pharmacy, Department of Organic Chemistry, Belgrade)
Popsavin Mirjana (Faculty of Science, Institute of Chemistry, Novi Sad)
Čanadi Janoš (Faculty of Science, Institute of Chemistry, Novi Sad)

The reactivity of the oxetane ring in 3,5-anhydro-1,2-O-cyclohexylidene- -D-xylofuranose (1) was exemplified by its regiospecific nucleophilic opening. The action of concentrated hydrobromic or hydroiodic acid on 1 resulted in the exclusive formation of the 5-deoxy-5-halo derivatives, while the action of acetyl chloride or acetyl bromide yielded the corresponding 3-O-acetyl-5-deoxy-5-halo derivatives in 70 - 90 % yield. Under strongly acidic reaction conditions, the protection of the cyclohexylidene acetal function remained intact.

Keywords: oxetane, sulfonyl esters, nucleophilic ring opening, D-xylofuranose derivatives