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Applications of protecting groups in the synthesis of surfactants, lipids, and related compounds
Author(s) -
Urata Kouichi,
Takaishi Naotake
Publication year - 1998
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-998-0010-x
Subject(s) - chemistry , dioxolane , alkyl , acetone , ether , organic chemistry , acetal , polyol , yield (engineering) , epoxide , catalysis , polyurethane , materials science , metallurgy
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.