Applications of protecting groups in the synthesis of surfactants, lipids, and related compounds

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. JSD 1, 73-82 (1998).

A perspective on the contribution of surfactants and lipids toward “Green Chemistry”: Present states and future potential

“…In summarizing the environmentally friendly methods discussed earlier and in discussing future potential of Green Chemistry based on surfactants and/or lipids, the first reaction to consider is the industrial-scale application of alkyl glycidyl ethers as a synthetic building block for deriving the corresponding ether lipids bearing an alkyl glyceryl ether skeleton (15,21,22,37). These ethers offer several possibilities for contributing to Green Chemistry.…”

“…The key compound in the preparation of these materials is commercially available 4-hydroxymethyl-1,3-dioxolane (glycerin ketal) prepared industrially by dehydration of glycerin with acetone in the presence of acid catalysts. A typical method for triglycerin monoalkyl ether synthesis is illustrated in Scheme 9 (37).…”

“…The O-alkylidene group is most useful for protect- Alkyl glyceryl ethers have been prepared on an industrial scale by the addition reaction of alkyl glycidyl ethers with excess acetone together in the presence of Lewis acid catalysts such as BF 3 -OEt 2 (Scheme 5) at a temperature of 20-40°C without additional heating (37).…”

“…1,3-Dioxolane compounds are useful protecting groups as intermediates for polyol-based fatty chemicals (37). Typical examples are given in Scheme 6.…”

Catalytic Transformation of Glycerol

“…Their use in newer synthetic approaches has been reviewed [43][44][45]. The presence of two free OH groups allows the introduction of much functionality for specific synthetic surfactants and specialty lipids.…”