Applications of protecting groups in the synthesis of surfactants, lipids, and related compounds |
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Authors: | Kouichi Urata Naotake Takaishi |
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Affiliation: | (1) Tokyo Research Laboratory, Kao Corporation, 131 Tokyo, Japan |
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Abstract: | Several types of alkyl ether lipids were prepared in high yield and high purity using protecting groups such as 1,3-dioxolane
compounds or allyl ethers. We also succeeded in the industrial production of alkyl glyceryl ethers using the reaction of alkyl
glycidyl ethers with acetone to give 1,3-dioxolane compounds, from which the desired alkyl glyceryl ethers were obtained in
high quantities. 1,3-Dioxolane (ketal) compounds based on acetone were used in the enzymatic preparation of monoglyceride
on an industrial scale. On the basis of these protecting groups, we extended our studies concerning both the preparations
and properties of novel polyol ether compounds, beginning with alkyl glycidyl ethers. Another typical property of surfactants
containing 1,3-dioxolane units and acetal is degradability under acidic conditions. Several types of destructible/cleavable
surfactants based on polyols, such as carbohydrates and polyethyleneglycol, were prepared. As for natural products containing
polyol skeletons, much attention has been paid to their molecular design, in which protecting groups such as 1,3-dioxolane
compounds or allyl ether have contributed to synthetic strategies. |
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Keywords: | Acetal allyl ether dioxolane compound glyceryl ether ketal lipid protecting group surfactant |
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