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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| Format: | Article |
| Language: | English |
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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 |
| _version_ | 1818945282653552640 |
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| author | Hadžić Pavle Vukojević Nada Popsavin Mirjana Čanadi Janoš |
| author_facet | Hadžić Pavle Vukojević Nada Popsavin Mirjana Čanadi Janoš |
| author_sort | Hadžić Pavle |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-20T07:56:38Z |
| format | Article |
| id | doaj.art-d69d23733d78499a89a63d7d5928a538 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-20T07:56:38Z |
| publishDate | 2001-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-d69d23733d78499a89a63d7d5928a5382022-12-21T19:47:41ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212001-01-016611810.2298/JSC0101001H0352-51390101001HNucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranoseHadžić Pavle0Vukojević Nada1Popsavin Mirjana2Čanadi Janoš3Faculty of Science, Institute of Chemistry, Novi SadFaculty of Pharmacy, Department of Organic Chemistry, BelgradeFaculty of Science, Institute of Chemistry, Novi SadFaculty of Science, Institute of Chemistry, Novi SadThe 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.http://www.doiserbia.nb.rs/img/doi/0352-5139/2001/0352-51390101001H.pdfoxetanesulfonyl estersnucleophilic ring openingd-xylofuranose derivatives |
| spellingShingle | Hadžić Pavle Vukojević Nada Popsavin Mirjana Čanadi Janoš Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose Journal of the Serbian Chemical Society oxetane sulfonyl esters nucleophilic ring opening d-xylofuranose derivatives |
| title | Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose |
| title_full | Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose |
| title_fullStr | Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose |
| title_full_unstemmed | Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose |
| title_short | Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose |
| title_sort | nucleophilic opening of the 3 5 anhydro ring in 1 2 o cyclohexylidene d xylofuranose |
| topic | oxetane sulfonyl esters nucleophilic ring opening d-xylofuranose derivatives |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2001/0352-51390101001H.pdf |
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