Synthesis of a novel D-glucose-conjugated 15-crown-5 ether with a spiro ketal structure

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 bis...

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Bibliographic Details
Published in:	Molecules (Basel, Switzerland) Vol. 13; no. 8; pp. 1840 - 1845
Main Authors:	Yamanoi, Takashi, Oda, Yoshiki, Muraishi, Hitomi, Matsuda, Sho
Format:	Journal Article
Language:	English
Published:	Switzerland MDPI AG 22-08-2008 MDPI
Subjects:	1-C-Vinylated glucose Crown ether Crown Ethers - chemical synthesis Crown Ethers - chemistry Furans Glucose Glucose - chemistry Glucosides Glycosylation Oxidation Spiro Compounds Spiroketal
Online Access:	Get full text
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules13081840