Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure

Autor: Sho Matsuda, Hitomi Muraishi, Yoshiki Oda, Takashi Yamanoi
Jazyk: angličtina
Rok vydání: 2008
Předmět:
Zdroj: Molecules, Vol 13, Iss 8, Pp 1840-1845 (2008)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules13081840
Popis: Abstract: This paper describes a synthetic approach to a novel D-glucose-conjugated 15-crown-5 ether having a spiroketal structure starting from a 1-C-vinylated glucose derivative. The approach consists of the glycosylation of the vinylated glucose derivative to give an ethyleneoxy spacer derivative using bismuth(III) triflate, the conversion of the 1-C-vinyl group of the glucoside produced into a carboxylic acid group, and the intramolecular condensation between the carboxyl group and the terminal hydroxyl group in the ethyleneoxy spacer. A D-glucose-conjugated 15-crown-5 ether having a unique spiroketal structure was thus successfully synthesized.
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