Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene- -D-xylofuranose
Autor: | Hadžić Pavle, Vukojević Nada, Popsavin Mirjana, Čanadi Janoš |
---|---|
Jazyk: | angličtina |
Rok vydání: | 2001 |
Předmět: | |
Zdroj: | Journal of the Serbian Chemical Society, Vol 66, Iss 1, Pp 1-8 (2001) |
Druh dokumentu: | article |
ISSN: | 0352-5139 1820-7421 |
DOI: | 10.2298/JSC0101001H |
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: | Directory of Open Access Journals |
Externí odkaz: |
načítá se...