A convenient synthesis of long‐chain 1‐O‐Alkyl glyceryl ethers

Urata, Kouichi; Yano, Shinji; Kawamata, Akira; Takaishi, Naotake; Inamoto, Yoshiaki

doi:10.1007/bf02542409

Cited by 36 publications

(34 citation statements)

References 15 publications

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“…More recently, Urata et al (1988) have achieved the synthesis of 1-O-alkylglycerols via prior preparation of alkyl glycidyl ethers (1-O-alkyl-2,3-epoxypropanes), by coupling epichlorohydrin with fatty alcohols using a quaternary ammonium salt as phase transfer catalyst in an alkaline water-hexane solvent system, resulting in 80% yield for the oleyl chain. The epoxide was then converted to the corresponding acetonide or diacetate by treatment with acetone and boron trifluoride etherate (BF 3 ·Et 2 O) or acetic acid anhydride with a tertiary amine, followed by hydrolysis, in 63 and 67% overall yields, respectively.…”

Section: Chemical Synthesismentioning

confidence: 99%

Ether lipids

Magnusson

Haraldsson

2011

Chemistry and Physics of Lipids

124

119

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The naturally occurring 1-O-alkyl-sn-glycerols and their methoxylated congeners, 1-O-(2'-methoxyalkyl)-sn-glycerols, are biologically active compounds, ubiquitously found in nature as diacyl glyceryl ether lipids and phosphoether lipids. The chief objective of this article is to provide a comprehensive and up to date review on such ether lipids. The occurrence and distribution of these compounds in nature are extensively reviewed, their chemical structure and molecular variety, their biosynthesis and chemical synthesis and, finally, their various biological effects are described and discussed. An unprecedented biosynthesis of the 2'-methoxylated alkylglycerols is proposed. The first synthesis of enantiopure (Z)-(2'R)-1-O-(2'-methoxyhexadec-4'-enyl)-sn-glycerol, the most prevalent 2'-methoxylated type alkylglycerol present in cartilaginous fish, is described. It was accomplished by a highly convergent five step process.

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Section: Chemical Synthesismentioning

confidence: 99%

Ether lipids

Magnusson

Haraldsson

2011

Chemistry and Physics of Lipids

124

119

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“…A transesterification reaction 15 using 1,3-propanediol in CHCl3 promoted the cleavage of five-membered ring boronates (7, 8, 9) furnishing after flash chromatography purification the desired natural products chimyl (1), batyl (2) and selachyl (3) alcohols in 87%, 85%, 77% yields. (Scheme 1) Compared to other procedures described in the present literature [13,16,17,18,19,20,21,22] the synthesis of chimyl (1), batyl (2) and selachyl (3) alcohols described herein is an efficient synthetic approach, which presents a straightforward chemical transformation of an epoxide function to cyclic phenylboronate intermediates.…”

Section: IIImentioning

confidence: 99%

Synthesis of natural ether lipids and 1-O-hexadecylglycero-arylboronates via an epoxide-ring opening approach: Potential antifouling additives to marine paint coatings

Nascimento¹,

Monteiro²,

Braga³

et al. 2018

IJAERS

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Abstract-In this paper a new and efficient procedure for the synthesis of natural 1-O-alkyl glyceryl ethers such as chimyl (1), batyl (2) and selachyl (3) is described. Alkyl glycidyl ethers (4-6) were synthetized using solvents free reactions. A stereospecific ring-opening reaction of epoxides (4-6) with phenylboronic acid in dry dioxane, giving rise to cyclic arylboronates in high yields (90-98%).Seven new 1-O-hexadecylglycero-arylboronates (7-f) and chimyl alcohol (1) were evaluated in laboratory antifouling assays.

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“…Another synthetic target molecule is an important intracellular signaling molecule. L-α-Phosphatidyl-D-myo-inositol-3,4,5-triphosphate[PtIns (3,4,5)p 3 ] is an in vivo product of phosphoinositide 3-OH-kinase (PI3K) and was first isolated by Traynor-Kaplan et al (48) from agonist-stimulated human neutrophils in 1988. Certain studies have suggested that PtIns(3,4,5)P 3 and PI3K are both involved in a new intracelullar signaling system independent of the PtIns(4,5)P 2 -based pathway (Scheme 17).…”

Section: Scheme 11mentioning

confidence: 99%

“…To this end, we have previously reported on the industrial scale preparation of alkyl glyceryl ethers, pseudoceramides, and related compounds through the combination of protecting groups and the phase-transfer catalytic (PTC) reaction, as shown in Scheme 1 (4)(5)(6)(7)(8)(9).…”

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confidence: 99%

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

Urata

Takaishi

1998

J Surfact & Detergents

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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).

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A convenient synthesis of long‐chain 1‐O‐Alkyl glyceryl ethers

Cited by 36 publications

References 15 publications

Ether lipids

Ether lipids

Synthesis of natural ether lipids and 1-O-hexadecylglycero-arylboronates via an epoxide-ring opening approach: Potential antifouling additives to marine paint coatings

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

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