ChemInform Abstract: SYNTHESES OF SUBSTITUTED GLYCEROL ETHERS

Abstract

Nach gebräuchlichen Methoden wurden 35 Glycerinäther des Typs′(VII) synthetisiert, wie z.B. der Äther (VI) aus Isopentylbromid (I) über die Stufen (II)‐(V).

Ether lipids

“…It was started with the regioselective opening of (R)-epichlorohydrin with tridec-1-ynyllithium, obtained by treatment with n-butyllithium, in the presence of boron trifluoride according to Yamaguchi and Hirao (1983), affording (R)-1-chlorohexadec-4-yn-2-ol 34 in 50% yields and 98% ee -sn-glycerol 14 in 99% yields and 27% overall yields from (R)-epichlorohydrin. The right stereochemistry of 14 was confirmed (Magnusson and Haraldsson, 2010) by firstly, comparing the 1 H NMR spectrum of 13, obtained by hydrogenation of 14, with that of 13 from literature (Stallberg, 1990), to confirm the type of diastereomer, and secondly, by comparison of the optical activities of the afforded 13 and 14 with those found in literature (Stallberg, 1975(Stallberg, , 1990, to confirm the type of enantiomer.…”

“…Following the same methodology, Stallberg (1975) synthesized various substituted alkylglycerols, and like in the synthesis of 1-O-(2 -methoxyhexadecyl)glycerol, he employed substituted alkyl tosylates obtained via reduction of the corresponding acid derivatives. Among the substituted alkylglycerols that Stallberg synthesized was the monounsaturated 2 -methoxylated alkylglycerol (Z)-1-O-(2 -methoxyhexadec-4 -enyl)glycerol 28 obtained as a mixture of 4 stereoisomers (Scheme 6).…”