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Molecules 2008, 13(8), 1840-1845; doi:10.3390/molecules13081840
Article

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

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Received: 18 July 2008; in revised form: 12 August 2008 / Accepted: 19 August 2008 / Published: 22 August 2008
(This article belongs to the Special Issue Spiro Compounds)
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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 Crown ether; Spiroketal; 1-C-Vinylated glucose; Glycosylation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA 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(8):1840-1845.

Chicago/Turabian Style

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.



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