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...
Main Authors: | , , , |
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Format: | Article |
Language: | English |
Published: |
Serbian Chemical Society
2001-01-01
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Series: | Journal of the Serbian Chemical Society |
Subjects: | |
Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2001/0352-51390101001H.pdf |
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. |
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ISSN: | 0352-5139 1820-7421 |