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Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan
* Author to whom correspondence should be addressed.
Received: 18 July 2008; in revised form: 12 August 2008 / Accepted: 19 August 2008 / Published: 22 August 2008
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.
Keywords: Crown ether; Spiroketal; 1-C-Vinylated glucose; Glycosylation
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MDPI and ACS Style
Yamanoi, T.; Oda, Y.; Muraishi, H.; Matsuda, S. Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure. Molecules 2008, 13, 1840-1845.
Yamanoi T, Oda Y, Muraishi H, Matsuda S. Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure. Molecules. 2008; 13(8):1840-1845.
Yamanoi, Takashi; Oda, Yoshiki; Muraishi, Hitomi; Matsuda, Sho. 2008. "Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure." Molecules 13, no. 8: 1840-1845.