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.
Highlights
Crown ether molecules with saccharide moieties are interesting as chiral phase-transfer catalysts
Many saccharidebased crown ether molecules have been synthesized by chemical procedures [5,6,7]
For the purpose of further exploring the utility of the 1-C-vinylated sugars, we investigated the synthesis of a novel crown ether molecule from a 1-C-vinylated D-glucose derivative 1
Summary
Crown ether molecules with saccharide moieties are interesting as chiral phase-transfer catalysts [1,2]. As these chemical methods bind the original hydroxyl groups of the saccharide with an ethyleneoxy spacer, they cannot produce crown ether compounds having spiroketal structures. This paper describes our synthetic approach to a novel 15-crown-5 ether 2 having a spiroketal structure from a 1-C-vinylated glucose derivative (1).
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