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:	oxetane sulfonyl esters nucleophilic ring opening d-xylofuranose derivatives Chemistry QD1-999
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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