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

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 / Revised: 12 August 2008 / Accepted: 19 August 2008 / Published: 22 August 2008
(This article belongs to the Special Issue Spiro Compounds)
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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. View Full-Text
Keywords: Crown ether; Spiroketal; 1-C-Vinylated glucose; Glycosylation Crown ether; Spiroketal; 1-C-Vinylated glucose; Glycosylation

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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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