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

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, whil...

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Bibliographic Details
Main Authors: Hadžić Pavle, Vukojević Nada, Popsavin Mirjana, Čanadi Janoš
Format: Article
Language:English
Published: Serbian Chemical Society 2001-01-01
Series:Journal of the Serbian Chemical Society
Subjects:
Online Access:http://www.doiserbia.nb.rs/img/doi/0352-5139/2001/0352-51390101001H.pdf
Description
Summary: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.
ISSN:0352-5139
1820-7421