Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose
| Autor: | J Janos Canadi, Nada Vukojević, Pavle Hadzic, Mirjana Popsavin |
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| Rok vydání: | 2001 |
| Předmět: |
d-xylofuranose derivatives
Chemistry Acetal oxetane General Chemistry nucleophilic ring opening Ring (chemistry) Oxetane Medicinal chemistry sulfonyl esters lcsh:Chemistry Acetyl bromide chemistry.chemical_compound lcsh:QD1-999 Nucleophile Acetyl chloride Yield (chemistry) Organic chemistry Reactivity (chemistry) |
| Zdroj: | Journal of the Serbian Chemical Society, Vol 66, Iss 1, Pp 1-8 (2001) |
| ISSN: | 1820-7421 0352-5139 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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