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
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