Identifizierung der Glycidyläther Bis-phenyl- und Bis-α-naphthylurethane der α-Alkyl(aryl)äther des Glycerins

Glyceryl-ether monooxygenase [EC 1.14.16.5]. A microsomal enzyme of ether lipid metabolism

“…This procedure, however, was unsatisfactory for making ethers in which the alkyl chain was unsaturated, e.g., selachyl alcohol (see 2), as it would hydroxylate the double bond of the fatty chain as well. A procedure which did not suffer from this drawback (Scheme 5) started with the reaction of the fatty alcohol with epichlorohydrin (13) in the presence of boron trifluoride etherate at 55ЊC, 149 or stannic chloride, 150 which produced the intermediate 3-alkoxy-2-hydroxypropyl chloride (14). This was dehydrohalogenated with concentrated aqueous sodium hydroxide to the glycidic ether (15, 3-alkoxy-1,2-epoxypropane) which can be isolated in a pure state.…”

“…A number of ␣-alkyl glyceryl ethers (12) with short and long fatty straight or branched chains, as well as with aryl groups, were prepared by this synthesis 149 which was also used when the alkyl chain was unsaturated, e.g., racemic selachyl alcohol from oleyl alcohol. 138 In a useful modification of this synthesis epichlorohydrin was converted into 3-benzyloxy-1,2-epoxypropane (15, R ϭ PhCH 2 -) by this procedure, 149 or by direct reaction with sodium benzylate. 150 The benzyloxyepoxide was then transformed to 3-alkoxy-1-benzyloxypropan-2-ol by reaction with a fatty alcohol in the presence of boron trifluoride etherate.…”

Correlation Analysis of Ir and NMR Spectral Characteristics of Glycidyl Ethers

“…Alkyl glycidyl ethers were prepared according to the general procedure of Ulbrich 3 using BF 3 .etherate as catalyst. The epoxides were obtained after final rectification in 40-75% yields.…”

Glyceryl-ether Monooxygenase [EC 1.14.16.5J Part V: Some Aspects of the Stoichiometry

“…105°15 mmHg, prepared from epichlorohydrin and benzyl alcohol as before (15) and had a characteristic IH NMR spectrum (16)J and BF 3 ' Et20 (10 III of a solution of 1 rnl BFJ' EtzO in 50 rnl EbO) were heated in a sealed container at 60-65° for 1.5 h with stirring. The reaction was followed by TLC (alumina, with Et 2 0-nhexane 1:1 as eluent).…”